Carbon–Carbon Bond Formation by the Use of Chloroiodomethane as a C1 Unit. II. The Preparation and Synthetic Application of 1-Chloro-3-iodoheptane

Terminal alkenes, R–CH=CH2 (R=Et, n-Pr, n-Bu, n-Hex), were readily transformed into 1-chloro-3-iodoalkanes by the AIBN-induced free radical addition of chloroiodomethane. Thus, 1-chloro-3-iodoheptane was obtained from 1-hexene in an 88% yield; this in turn was allowed to react with dialkyl malonates in the presence of alkoxides in alcohols to give dialkyl 2-butylcyclobutane-1,1-dicarboxylates and dialkyl (E)-3-octene-1,1-dicarboxylates (7), either of which could be obtained preferentially by the choice of the experimental parameters. The olefinic product, 7, was further utilized for the synthesis of (E)-5-decenyl acetate and/or 1,4-nonanolide.