Abstract
Heating of formamide with an alkyl halide (with or without water) affords a mild, nonhydrolytic, high-yield synthesis of alcohols and formate esters. Yet the way in which substitution on the alkyl halide actually occurs remains occure. To explore this question, thermal reaction of 1-bromooctane (1a) with formamides (HC(O)NHR, R=H, Me; 2a, 2b) was studied quantitatively. Major products are 1-octanol (3) and n-octyl formate (5); minor products are 1-octene (4), di-n-octyl ether (6), and N-octylformamide (7, from 2a, only)
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