Kazumasa Takahashi, T. Nishizuka, H. Iida
Apr 13, 1982
Citations
0
Influential Citations
2
Citations
Journal
Synthetic Communications
Abstract
Abstract Several studies1 have been reported on the synthesis of 2,3-diphenyl-2-cyanooxiranes. Kohler and Brownla synthesized the oxirane in ca. 30% yield by reaction of desyl chloride with potassium cyanide in aqueous alcohol. However, the method which they employed seems to be rather complicated. Such reaction of desyl bromide with cyanide ion has not been studied in detail. We now report that cis- and trans-2,3-diphenyl-2-cyanooxiranes (2a-d and 3a-d) are conveniently obtained in good yields by reaction of 4′-substituted desyl bromide (1a-d) with 40% aqueous potassium cyanide in a mixture of dichloromethane and triethylbenzylammonium chloride (TEBAC); the total yield of 2c and 3c, for example, was as high as 86%. When cethyltriethylammonium bromide was used as a