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Journal articles on the topic 'Ketene dithioacetal'

Author: Grafiati

Published: 22 February 2025

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1

Yu, Haifeng, Dewen Dong, Yan Ouyang, and Qun Liu. "Chemoselective thioacetalization with odorless 2-(1,3-dithian-2-ylidene)-3-oxobutanoic acid as a 1,3-propanedithiol equivalent." Canadian Journal of Chemistry 83, no. 10 (October 1, 2005): 1741–45. http://dx.doi.org/10.1139/v05-184.

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Odorless 2-(1,3-dithian-2-ylidene)-3-oxobutanoic acid (1c) was prepared and investigated in the thioacetalization of carbonyl compounds as a 1,3-propanedithiol equivalent. The results showed that the thioacetalization of various carbonyl compounds 2 with 1c proceeded smoothly and afforded the corresponding dithioacetals 3 in high yields (up to 99%) in the presence of acetyl chloride at room or reflux temperatures. Moreover, the thioacetalization exhibited high chemoselectivity between aldehydes and ketones. Key words: chemoselectivity, 2-(1,3-dithian-2-ylidene)-3-oxobutanoic acid, α-oxo ketene dithioacetal, 1,3-propanedithiol equivalent, thioacetalization.

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2

TOMINAGA, Yoshinori, Yoshiki MATSUOKA, Chizuko KAMIO, and Akira HOSOMI. "Ketene dithioacetals in organic synthesis: Synthesis of silyl ketene dithioacetal and some reactions with substituted benzaldehydes." CHEMICAL & PHARMACEUTICAL BULLETIN 37, no. 11 (1989): 3168–70. http://dx.doi.org/10.1248/cpb.37.3168.

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3

Pan, Ling, Xihe Bi, and Qun Liu. "Recent developments of ketene dithioacetal chemistry." Chem. Soc. Rev. 42, no. 3 (2013): 1251–86. http://dx.doi.org/10.1039/c2cs35329f.

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4

Huang, Yu-Chieh, An Nguyen, Simone Gräßle, Sylvia Vanderheiden, Nicole Jung, and Stefan Bräse. "Addition of dithi(ol)anylium tetrafluoroborates to α,β-unsaturated ketones." Beilstein Journal of Organic Chemistry 14 (February 26, 2018): 515–22. http://dx.doi.org/10.3762/bjoc.14.37.

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In the presented study, dithi(ol)anylium tetrafluoroborates are added to α,β-unsaturated ketones in a Michael-type reaction yielding diverse substituted ketene diothi(ol)anes. The reactions proceed at room temperature in 1 or 13 h without the need of further additives. The presented procedure is in particular useful for dithi(ol)anylium tetrafluoroborates without electron-withdrawing groups in α-position. This is advantageous with respect to previous approaches, which were limited to the use of ketene dithioacetals substituted with electron-withdrawing groups. Aiming for the systematic investigation of possible steric and electronic influences on the outcome of the reaction, various combinations of electrophiles and nucleophiles were used and the results of the reactions were compared based on the type of the used dithioacetal. The scope of the presented procedure is shown with four additional transformations including the use of additional electrophiles and nucleophiles, the use of a chiral auxiliary and subsequent reduction of selected products. Additionally, we extended the reaction to the synthesis of diene dithiolanes by addition of an ynone to α-alkyl or aryl-substitued dithiolanylium TFBs.

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5

Wang, Xiaolun, Xu Chen, Hongzhen Lian, Yi Pan, and Yaozeng Shi. "Syntheses Of Ketene Dithioacetal Derivatives Of 2,5-Piperazinedione." Synthetic Communications 29, no. 9 (May 1999): 1553–60. http://dx.doi.org/10.1080/00397919908086135.

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6

Pan, Ling, Xihe Bi, and Qun Liu. "ChemInform Abstract: Recent Developments of Ketene Dithioacetal Chemistry." ChemInform 44, no. 23 (May 16, 2013): no. http://dx.doi.org/10.1002/chin.201323222.

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7

Tominaga, Yoshinori, and Yoshiro Matsuda. "Synthesis of heterocyclic compounds using nitro ketene dithioacetal." Journal of Heterocyclic Chemistry 22, no. 4 (July 1985): 937–49. http://dx.doi.org/10.1002/jhet.5570220401.

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8

Anand, Aditi, Navjeet Kaur, and Dharma Kishore. "An Efficient One Pot Protocol to the Annulation of Face “d” of Benzazepinone Ring with Pyrazole, Isoxazole, and Pyrimidine Nucleus through the Corresponding Oxoketene Dithioacetal Derivative." Advances in Chemistry 2014 (August 6, 2014): 1–5. http://dx.doi.org/10.1155/2014/358153.

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A highly facile single step approach to the annulation of face “d” of benzazepinone nucleus with pyrazole, isoxazole, and pyrimidine ring has been described. The annulation proceeded smoothly on the reaction of oxoketene dithioacetal derivative 3 with (i) NH2–NH2·H2O, (ii) NH2OH·HCl, (iii) acetamidine hydrochloride, (iv) guanidine nitrate, (v) urea, and (vi) thiourea which yielded the pyrazolo, isoxazolo, and pyrimido annulated analogues of benzazepinone 4–9, respectively, in acceptable yields. The 4-ketene dithioacetal analogue of 7-fluorobenzo[b]azepine-2,5-dione (3) was in turn obtained from the reaction of 7-fluoro-3,4-dihydro-1H-benzo[b]azepine-2,5-dione (2) (with CS2 + CH3I in presence of t-BuOK). 7-Fluoro-3,4-dihydro-1H-benzo[b]azepine-2,5-dione (2) resulted from the acylation of p-fluoroaniline with succinyl chloride followed by cyclocondensation of the later with polyphosphoric acid (PPA).

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9

Murakami, Kei, Hideki Yorimitsu, and Atsuhiro Osuka. "Practical and Scalable Syntheses of Substituted Ketene Dithioacetal Monoxides." Bulletin of the Chemical Society of Japan 86, no. 10 (October 15, 2013): 1193–95. http://dx.doi.org/10.1246/bcsj.20130148.

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10

Murakami, Kei, Hideki Yorimitsu, and Atsuhiro Osuka. "Practical and Scalable Syntheses of Substituted Ketene Dithioacetal Monoxides." Bulletin of the Chemical Society of Japan 87, no. 3 (March 15, 2014): 441. http://dx.doi.org/10.1246/bcsj.20140021.

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11

Lamberth, Clemens, Julien Gagnepain, Stephane Jeanmart, Damien Bonvalot, and Olivier Jacob. "Synthesis of Conformationally Locked and C-Linked Analogues of Imidazole-Based Ketene Dithioacetal Fungicides." Synlett 30, no. 01 (December 3, 2018): 59–62. http://dx.doi.org/10.1055/s-0037-1610341.

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First examples with the unknown tricyclic 4,8b-dihydro-3aH-indeno[1,2-d][1,3]dithiole ring system have been prepared. Also, imidazoles linked in ring position 5 to a ketene dithioacetal and 1,3-dithiane derivatives with an exocyclic cyano- and imidazole-substituted C–C double bond are completely new. All these compounds are either conformationally locked, C-linked or six-ring analogues of the antifungal agent luliconazole. Synthesis and fungicidal activity of these sterol biosynthesis inhibitors are reported.

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12

Sun, Yongmao, Bin Liu, Jeff Kao, D. Andre' d'Avignon, and Kevin D. Moeller. "Anodic Cyclization Reactions: Reversing the Polarity of Ketene Dithioacetal Groups." Organic Letters 3, no. 11 (April 28, 2001): 1729–32. http://dx.doi.org/10.1021/ol015925d.

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13

Wang, Xiaolun, Xu Chen, Hongzhen Lian, Yi Pan, and Yaozeng Shi. "ChemInform Abstract: Syntheses of Ketene Dithioacetal Derivatives of 2,5-Piperazinedione." ChemInform 30, no. 30 (June 14, 2010): no. http://dx.doi.org/10.1002/chin.199930166.

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14

Tominaga, Yoshinori, Yoshihide Shiroshita, and Akira Hosomi. "Synthesis of 2-methylthioindolizine-3-carbonitriles using nitro ketene dithioacetal." Journal of Heterocyclic Chemistry 25, no. 6 (November 1988): 1745–49. http://dx.doi.org/10.1002/jhet.5570250627.

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15

Khunt, Hasmukh R., Piyush P. Pipaliya, Satish M. Ghelani, Jayesh S. Babariya, and Yogesh T. Naliapara. "Synthesis and Characterization of Fully Substituted Pyrimidines by Using Ketene Dithioacetal as Potent Antimicrobial Agent." International Letters of Chemistry, Physics and Astronomy 24 (December 2013): 134–41. http://dx.doi.org/10.18052/www.scipress.com/ilcpa.24.134.

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Various ketene dithioacetals of acetoacetanilides were reacted with guanidine nitrate in the presence of base to produce the 2-amino-4-isopropyl-6-alkoxy-N-arylpyrimidine-5-carboxamide derivatives with good yields. All the synthesized compounds were characterized by mass, NMR and IR and also evaluated for antimicrobial activity against five different bacterial and fungal strains. The compounds 4i, 4k and 4l has found comparatively good active against all the bacterial strains.

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16

Khunt, Hasmukh R., Piyush P. Pipaliya, Satish M. Ghelani, Jayesh S. Babariya, and Yogesh T. Naliapara. "Synthesis and Characterization of Fully Substituted Pyrimidines by Using Ketene Dithioacetal as Potent Antimicrobial Agent." International Letters of Chemistry, Physics and Astronomy 24 (December 26, 2013): 134–41. http://dx.doi.org/10.56431/p-z179r2.

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Various ketene dithioacetals of acetoacetanilides were reacted with guanidine nitrate in the presence of base to produce the 2-amino-4-isopropyl-6-alkoxy-N-arylpyrimidine-5-carboxamide derivatives with good yields. All the synthesized compounds were characterized by mass, NMR and IR and also evaluated for antimicrobial activity against five different bacterial and fungal strains. The compounds 4i, 4k and 4l has found comparatively good active against all the bacterial strains.

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17

Murakami, Kei, Hideki Yorimitsu, and Atsuhiro Osuka. "ChemInform Abstract: Practical and Scalable Syntheses of Substituted Ketene Dithioacetal Monoxides." ChemInform 45, no. 46 (October 30, 2014): no. http://dx.doi.org/10.1002/chin.201446096.

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18

Farag, Awatef A., Mohamed F. El Shehry, Samir Y. Abbas, Safaa N. Abd-Alrahman, Abeer A. Atrees, Hiaat Z. Al-basheer, and Yousry A. Ammar. "Synthesis of pyrazoles containing benzofuran and trifluoromethyl moieties as possible anti-inflammatory and analgesic agents." Zeitschrift für Naturforschung B 70, no. 7 (July 1, 2015): 519–26. http://dx.doi.org/10.1515/znb-2015-0009.

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AbstractSearching for new anti-inflammatory and analgesic agents, we have prepared a series of novel pyrazoles containing benzofuran and trifluoromethyl moieties. The pyrazole derivatives have been synthesized via two routes starting from 5-(3-(trifluoromethyl)phenyl azo) salicylaldehyde. The first route involved the synthesis of 2-acetylbenzofuran and then treatment with aldehydes to afford the corresponding chalcones. The cyclization of the latter chalcones with hydrazine hydrate led to the formation of new pyrazoline derivatives. The second route involved the synthesis of benzofuran-2-carbohydrazide and then treatment with formylpyrazoles, chalcones and ketene dithioacetal derivatives to afford the corresponding pyrazole derivatives. Some of the synthesized compounds exhibited anti-inflammatory and analgesic activities.

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19

Negroni, B., A. Botrel, M. Hérail, and A. Proutière. "Conformational study and ground state dipole moments of two ketene dithioacetal compounds." Journal of Molecular Structure 405, no. 2-3 (March 1997): 133–38. http://dx.doi.org/10.1016/s0022-2860(96)09603-2.

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20

Sun, Yongmao, Bin Liu, Jeff Kao, D. Andre d'Avignon, and Kevin D. Moeller. "ChemInform Abstract: Anodic Cyclization Reactions: Reversing the Polarity of Ketene Dithioacetal Groups." ChemInform 32, no. 38 (May 24, 2010): no. http://dx.doi.org/10.1002/chin.200138040.

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21

Molinari, Aurora, Alfonso Oliva, Lucá Sánchez, and Arturo San Feliciano. "Ketene dithioacetal derivatives of 1-phenyl-3,5-dioxopyrazolidine. Synthesis and NMR characterization." Journal of Heterocyclic Chemistry 34, no. 4 (July 1997): 1297–99. http://dx.doi.org/10.1002/jhet.5570340434.

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22

Bhale, Pravin S., Babasaheb P. Bandgar, Sakharam B. Dongare, Sadanand N. Shringare, Dnyaneshwar M. Sirsat, and Hemant V. Chavan. "Ketene dithioacetal mediated synthesis of 1,3,4,5-tetrasubstituted pyrazole derivatives and their biological evaluation." Phosphorus, Sulfur, and Silicon and the Related Elements 194, no. 8 (January 25, 2019): 843–49. http://dx.doi.org/10.1080/10426507.2019.1565760.

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23

Rao, Varanosi Pushkara, Y. M. Cai, and Alex K.-Y. Jen. "Ketene dithioacetal as a π-electron donor in second-order nonlinear optical chromophores." J. Chem. Soc., Chem. Commun., no. 14 (1994): 1689–90. http://dx.doi.org/10.1039/c39940001689.

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24

Sakurai, Osamu, and Hiroshi Horikawa. "A new synthetic method of 1β-methylcarbapenems utilizing the ketene dithioacetal-terminated cyclization." Tetrahedron Letters 37, no. 43 (October 1996): 7811–14. http://dx.doi.org/10.1016/0040-4039(96)01785-6.

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25

Armitt, David J., Michael I. Bruce, Brian W. Skelton, and Allan H. White. "Reactions of Alkynyl−Ruthenium Complexes with the Ketene Dithioacetal, (MeS)2CC(CN)2." Organometallics 27, no. 14 (July 2008): 3556–63. http://dx.doi.org/10.1021/om7011437.

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26

Fathalla, O. A. "Synthesis of new pyrazolo[1,5-a]pyrimidine derivative using 5-aminouracil and ketene dithioacetal." Archives of Pharmacal Research 22, no. 6 (December 1999): 571–74. http://dx.doi.org/10.1007/bf02975328.

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27

Yavari, Issa, Jamil Sheykhahmadi, Hamed Saffarian, and Mohammad Reza Halvagar. "Nef-isocyanide-Perkow access to novel pyrazolone derivations containing a cyclic ketene dithioacetal moiety." Synthetic Communications 49, no. 3 (January 17, 2019): 456–62. http://dx.doi.org/10.1080/00397911.2018.1560474.

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28

Veenstra, G. E., and B. Zwanenburg. "Chemistry of sulfines. Part 32. Synthesis and reactions of (phenylsulfonyl)ketene dimethyl dithioacetal monoxide." Recueil des Travaux Chimiques des Pays-Bas 95, no. 9 (September 2, 2010): 202–5. http://dx.doi.org/10.1002/recl.19760950903.

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29

MOLINARI, A., A. OLIVA, L. SANCHEZ, and A. SAN FELICIANO. "ChemInform Abstract: Ketene Dithioacetal Derivatives of 1-Phenyl-3,5-dioxopyrazolidine. Synthesis and NMR Characterization." ChemInform 29, no. 2 (June 24, 2010): no. http://dx.doi.org/10.1002/chin.199802112.

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30

Hewson, Alan T., Stewart K. Richardson, and David A. Sharpe. "Acid catalysed reactions of aryl ketene dithioacetal S-oxides: synthesis of chloroketene thioacetals and thioesters." Journal of the Chemical Society, Perkin Transactions 1, no. 11 (1990): 2967. http://dx.doi.org/10.1039/p19900002967.

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31

Lee, Ge Hyeong, and Chwang Siek Pak. "Synthesis of 2-Methylthio-4H-4-chromenones via Ketene Dithioacetal in the One-Pot Reaction." Synthetic Communications 29, no. 14 (July 1999): 2539–45. http://dx.doi.org/10.1080/00397919908086262.

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32

Ogura, Katsuyuki, Atsushi Yanagisawa, Takeo Fujino, and Kazumasa Takahashi. "An efficient acceptor of 1-hydroxy(or alkoxy)alkyl radicals – ketene dithioacetal S,S-dioxide –." Tetrahedron Letters 29, no. 42 (1988): 5387–90. http://dx.doi.org/10.1016/s0040-4039(00)82875-0.

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33

Shingate, Bapurao B., Braja G. Hazra, Vandana S. Pore, Rajesh G. Gonnade, and Mohan M. Bhadbhade. "Ionic hydrogenation of C-20, 22-ketene dithioacetal: stereoselective synthesis of steroidal C (20R) aldehydes." Chemical Communications, no. 19 (2004): 2194. http://dx.doi.org/10.1039/b407952c.

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34

Narasaka, Koichi, Takanori Shibata, and Yujiro Hayashi. "Acid-Promoted Reactions of Schiff’s Bases with Ketene Dithioacetal, Vinyl Sulfides, and 1,2-Propadienyl Sulfides." Bulletin of the Chemical Society of Japan 65, no. 5 (May 1992): 1392–96. http://dx.doi.org/10.1246/bcsj.65.1392.

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35

Okuyama, Tadashi, and Takayuki Fueno. "Acid-catalyzed hydrolysis of a .gamma.-(hydroxyalkyl) ketene dithioacetal. A cyclic intermediates and product distribution." Journal of Organic Chemistry 52, no. 8 (April 1987): 1405–8. http://dx.doi.org/10.1021/jo00384a004.

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36

Fiala, A., A. Chibani, A. Darchen, A. Boulkamh, and K. Djebbar. "Investigations of the inhibition of copper corrosion in nitric acid solutions by ketene dithioacetal derivatives." Applied Surface Science 253, no. 24 (October 2007): 9347–56. http://dx.doi.org/10.1016/j.apsusc.2007.05.066.

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37

RAO, V. P., Y. M. CAI, and A. K. Y. JEN. "ChemInform Abstract: Ketene Dithioacetal as a π-Electron Donor in Second-Order Nonlinear Optical Chromophores." ChemInform 25, no. 49 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199449185.

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38

Kinoshita, Jun, Alexandre Baralle, Akira Yoshida, Tomoyuki Yanagi, Keisuke Nogi, and Hideki Yorimitsu. "A Route to Indoles via Modified Fischer Indole Intermediates from Sulfonanilides and Ketene Dithioacetal Monoxides." Asian Journal of Organic Chemistry 9, no. 10 (September 2020): 1655–59. http://dx.doi.org/10.1002/ajoc.202000397.

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39

SAKURAI, O., and H. HORIKAWA. "ChemInform Abstract: A New Synthetic Method of 1β-Methylcarbapenems Utilizing the Ketene Dithioacetal-Terminated Cyclization." ChemInform 28, no. 6 (August 4, 2010): no. http://dx.doi.org/10.1002/chin.199706227.

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40

Gonzalez-Cameno, Ana Maria, Mariella Mella, Maurizio Fagnoni, and Angelo Albini. "ChemInform Abstract: Photochemical Alkylation of Ketene Dithioacetal S,S-Dioxides. An Example of Captodative Olefin Functionalization." ChemInform 31, no. 18 (June 8, 2010): no. http://dx.doi.org/10.1002/chin.200018062.

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41

Wang, Mang, Shaoguang Sun, Deqiang Liang, Bangyu Liu, Ying Dong, and Qun Liu. "Sulfuric Acid-Catalyzed Regioselective Alkylation of Indoles and β-Naphthols with Ketene Dithioacetal-Based Allylic Alcohols." European Journal of Organic Chemistry 2011, no. 13 (March 14, 2011): 2466–73. http://dx.doi.org/10.1002/ejoc.201001487.

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42

Niwano, Yoshimi, Tetsuto Ohmi, Akira Seo, Hiroki Kodama, Hiroyasu Koga, and Atsusi Sakai. "Lanoconazole and Its Related Optically Active Compound NND-502: Novel Antifungal Imidazoles with a Ketene Dithioacetal Structure." Current Medicinal Chemistry -Anti-Infective Agents 2, no. 2 (June 1, 2003): 147–60. http://dx.doi.org/10.2174/1568012033483097.

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43

Chavan, Satish M., Raghunath B. Toche, Vasant M. Patil, Pankaj B. Aware, and Poonam S. Patil. "Reactions of ketene dithioacetal for a new versatile synthesis of 4,5-substituted 3-aminothiophene-2-carboxylate derivatives." Journal of Sulfur Chemistry 37, no. 4 (March 28, 2016): 426–37. http://dx.doi.org/10.1080/17415993.2016.1156117.

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44

Suzuki, Keisuke, Toshiyuki Masuda, Yoshimasa Fukazawa, and Gen-ichi Tsuchihashi. "C(2)-stereocontrol of δ-lactones acid-catalyzed cyclization of ketene dithioacetal having an internal hydroxyl group." Tetrahedron Letters 27, no. 31 (January 1986): 3661–64. http://dx.doi.org/10.1016/s0040-4039(00)84875-3.

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45

Lee, Ge Hyeong, and Chwang Siek Pak. "ChemInform Abstract: Synthesis of 2-Methylthio-4H-4-chromenones via Ketene Dithioacetal in the One-Pot Reaction." ChemInform 30, no. 36 (June 13, 2010): no. http://dx.doi.org/10.1002/chin.199936157.

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46

NARASAKA, K., T. SHIBATA, and Y. HAYASHI. "ChemInform Abstract: Acid-Promoted Reactions of Schiff Bases with Ketene Dithioacetal, Vinyl Sulfides, and 1,2-Propadienyl Sulfides." ChemInform 23, no. 36 (August 21, 2010): no. http://dx.doi.org/10.1002/chin.199236067.

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47

Hewson, Alan T., Kevin Hughes, Stewart K. Richardson, David A. Sharpe, and Alan H. Wadsworth. "Acid-catalysed cyclisation of o-sulphonamido ketene dithioacetal S-oxides: a novel synthesis of the indole ring system." Journal of the Chemical Society, Perkin Transactions 1, no. 6 (1991): 1565. http://dx.doi.org/10.1039/p19910001565.

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48

Aggarwal, Varinder K., Juliet K. Barrell, Julia M. Worrall, and Rikki Alexander. "Highly Diastereoselective Epoxidation of Ketene Dithioacetal Dioxides: A New Approach to the Asymmetric Synthesis of α-Amino Amides." Journal of Organic Chemistry 63, no. 21 (October 1998): 7128–29. http://dx.doi.org/10.1021/jo9814896.

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49

Ogura, Katsuyuki, Takayuki Arai, Akio Kayano, and Motohiro Akazome. "Novel photochemical addition of aromatic aldehydes to ketene dithioacetal S,S-dioxides and its application to organic synthesis." Tetrahedron Letters 39, no. 49 (December 1998): 9051–54. http://dx.doi.org/10.1016/s0040-4039(98)02052-8.

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50

Młynarski, Jacek, and Anna Banaszek. "Synthetic approach to 3-deoxy-d-manno-oct-2-ulosonic acid (Kdo) α-disaccharides via a ketene dithioacetal." Tetrahedron: Asymmetry 11, no. 18 (September 2000): 3737–46. http://dx.doi.org/10.1016/s0957-4166(00)00371-2.

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