The Journal of Organic Chemistry

Addition of tert-butyldimethyl-or tert-butyldiphenylsilyl cyanide to hindered ketones

M Golinski, CP Brock, DS Watt

Index: Golinski, Miroslaw; Brock, Carolyn P.; Watt, David S. Journal of Organic Chemistry, 1993 , vol. 58, # 1 p. 159 - 164

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Citation Number: 45

Abstract

The addition of trimethylsilyl cyanide (TMSCN), tert-butyldimethylsilyl cyanide (TBDMSCN) or tert-butyldiphenylsilyl cyanide (TBDPSCN) to sterically hindered ketones proceeded in good yield under catalysis by Lewis acids (Zn12, CH2Cl2, 25 “C) or bases (KCN, 18-crown- 6, CH2C12, 25 OC). For example, the ZnI2-catalyzed addition of TBDMSCN to 2, 2- dimethylcyclohexanone (b), 2, 2, 6-trimethylcyclohexanone (30, and 2, 2, 6, 6- ...