Reaction of carbonyl oxides and thioketones. [3 + 2] Cycloaddition vs. oxygen atom transfer

Abstract

The ozonolysis of vinyl ethers (1a,b) in the presence of thioadamantan-2-one (4a) gave in each case the corresponding thin-ozonide (5a,b) in around 70% yield, whilst ozonolysis of a mixture of vinyl ethers (1a—c) and thiobenzophenone derivatives (4b—d) gave the corresponding thione-S-oxides (8b—d) in 15–30% yields, together with the benzophenones (6b—d).