81454-72-0Relevant articles and documents
Stereochemical Dependence of Base-Catalyzed Cleavage of Cyclic Peroxy Ketals
Snider, Barry B.,Shi, Zhongping,O'Neil, Steven V.,Kreutter, Kevin D.,Arakaki, Tracy L.
, p. 1726 - 1729 (1994)
Base-catalyzed decomposition of cyclic peroxy ketals 1c, 2c, 14, and 16 shows a strong stereochemical dependence.Isomers 2c and 16 with a pseudoequatorial hydrogen undergo a fast antiperiplanar E2 elimination to afford ene diones 4 and 17 that react further.Ester 1c, with a pseudoaxial hydrogen and a pseudoequatorial acetate side chain, reacts slowly to form the enolate, which undergoes an SN2 reaction to give epoxide 3.Peroxy ketals 14 and 15 are stable in base.Peroxy acetals 19 and 20 undergo a faster E2 elimination with loss of the pseudoequatorial acetal proton to provide alkoxide ester 21 that reacts further.