Abstract
Abstract Reaction of trimethylsilyl cyanide (TMSCN) with tropone and 2-phenyltropone in the presence of a catalytic amount of zinc iodide in dichloromethane afforded silyl ethers of 7-cyano-1,3,5-cycloheptatriene-1-ol (2a) and 2-phenyl-7-cyano-1,3,5-cycloheptatriene-1-ol (2b), respectively. On the other hand, reaction of TMSCN with 2-methoxytropone gave 2-cyanotropone. Upon hydrolysis, 2a, and 2b yielded 2-cyano-1,3,5-cycloheptatrien-1-ol (3a) and a tautomeric mixture of 2-cyano-7-phenyl-1,3,5-cycloheptatrien-1-ol (3b) and 2-cyano-7-phenyl-3,5-cycloheptadien-1-one (4b). Oxidation of 3a and the tautomeric mixture of 3b and 4b with selenium dioxide in dioxane afforded 2-cyanotropone and 2-cyano-7-phenyltropone, respectively.
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