The Reactions of α-Phosphoryl Sulfoxides With Ortho- and Para-Quinones. Synthesis of α,β -Unsaturated Sulfoxides and Aryl 1,2-x-Fused onto Furan Rings

Abstract

The reactions of α-phosphoryl sulfoxide 3 with o-quinones 1a-c were found to react in different pathways to give either the mono-olefin 4 (from 1a) or the corresponding [1,2-x]-fused dihydrofuran 8 (from 1b) or 9 (from 1c). Conversely, a completely different pattern of behaviour was observed for 3 toward the p-quinones 2a and 2b, whereby 2-(4-hydroxyaryl)-1,2-bis(methyl sulfoxide) ethyl diethyl phosphonate derivatives 11 and 12, respectively, were the products.