Thiacyanocarbons. 6. 1, 4-Dithiino [2, 3-c; 6, 5-c'] diisothiazole-3, 7-dicarbonitrile, isothiazole [3, 4-f][1, 2, 3, 4, 5] pentathiepine-8-carbonitrille, and disodium 5- …

SA Vladuchick, T Fukunaga, HE Simmons…

Index: Vladuchick, S. A.; Fukunaga, T.; Simmons, H. E.; Webster, O. W. Journal of Organic Chemistry, 1980 , vol. 45, # 25 p. 5122 - 5130

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Citation Number: 23

Abstract

of which contain 4n cyclic T electrons. The isothiazole 2 was obtained from 1 by a sulfur insertion-rearrangement reaction as shown in Scheme I. The ring opening to give the trans- dicyanoethylene intermediate 3l is assisted by resonance stabilization of the sulfide anion portion of the intermediate. This unusual reaction has now been extended to the synthesis of dicyano-1, 4-dithiino [2, 3-c; 6, 5-c'] diisothiazole 43 and 5-cyanoisothiazole dithiolate 7.* 3 ...