Synthesis of five-and six-membered 1,3,3-trimethyl-2-(trimethylsilyl) cycloalkenes: A novel preparation of alkyl/alkenyl/aryl 2,5,5-trimethyl-1- cyclopentenyl ketones

Abstract

1,3,3-trimethyl-2-(trimethylsilyl)cyclopentene and 1,3,3-trimethyl-2- -(trimethylsilyl)cyclohexene were prepared in good yields by the Wurtz-Fittig coupling reaction of the corresponding 2-iodo-1,3,3-trimethylcyclopentene and 2-chloro-1,3,3-trimethylcyclohexene with metallic sodium and chlorotrimethylsilane in anhydrous ether solvent. The Friedel-Crafts acylation reaction of 1,3,3-trimethyl-2-(trimethylsilyl)cyclopentene with six different acid chlorides and the novel preparation of six alkyl/alkenyl/aryl 2,5,5-trimethyl-1-cyclopentenyl ketones are reported.