Designing a non-volatile imaging switch for mass-persistent, chemically amplified photolithography: a model study

Abstract

An acid catalysed rearrangement that transforms a bicyclic lactone into a phenolic carboxylic acid has been tested for potential use in chemically amplified microlithographic imaging.

Total Synthesis of (±)-Antroquinonol D

“…After several unsuccessful attempts at reduction because of concomitant demethoxylation, we performed the Michael addition of dimethyl malonate on unsubstituted cyclohexadienones 19a and 19b prepared from 4-methoxyphenol As the elimination of the methoxy group was the main concern, cyclic acetal was used, and the Michael addition of dimethyl malonate with 19a provided conjugate adduct 20a (R = −CH 2 CH 2 −) in 53% yield (Scheme ). Chemoselective reduction of cyclohexenone 20a under Luche conditions followed by lactonization afforded the required lactone 21a in 47% yield .…”

“… As the elimination of the methoxy group was the main concern, cyclic acetal was used, and the Michael addition of dimethyl malonate with 19a provided conjugate adduct 20a (R = −CH 2 CH 2 −) in 53% yield (Scheme ). Chemoselective reduction of cyclohexenone 20a under Luche conditions followed by lactonization afforded the required lactone 21a in 47% yield . Much to our delight, the reduction and lactonization of dimethoxy ketal adduct 20b under the same conditions provided lactone 21b in 99% yield.…”