Direction of ring-opening of ring-substituted cyclopropyl(stannyloxy)methyl and cyclopropyl(hydroxy)methyl radicals: preferential formation of primary alkyl radicals

Abstract

cis- and trans-2-Methylcyclopropyl-stannyloxymethyl and -hydroxymethyl radicals (A) have been generated by treating either the corresponding tin alkoxides or alcohols with t-butoxyl radicals, or the corresponding ketones with tributylstannyl radicals. The e.s.r. spectra show that, at low temperature (< –60°C), the cis-(A) radicals undergo ring-opening to give principally secondary alkyl radicals, but the trans-(A) radicals give only primary alkyl radicals.