Investigations on the reactions of a carbonylcarbene with substituted 1,3-dioxepins

Talinli N., KARLIGA B., Anac O.

HELVETICA CHIMICA ACTA, vol.83, no.5, pp.966-971, 2000 (SCI-Expanded) identifier identifier


Several dioxepins were treated with dimethyl diazomalonate under bis(acetylacetonato)copper(II) catalysis. The 4,7-dihydro-2-methyl-1,3-dioxepin (1a) gave oxonium ylide originated products and a cyclopropane derivative (see 3a and 2a. resp.. in Scheme 3b). However, the 2,2-dimethyl derivative 1b of 1,3-dioxepin yielded only the cyclopropanation product 2b, (Scheme 3.b), whereas 4,5-dihydro-2-methyl-1,3-dioxepin (9) gave the furanofuran derivative 10 (Scheme 4).