Synthetic strategies towards the carbenoid reactions of α, β -acetylenic carbonyls

Abstract

Catalytic reactions of α, β -conjugated carbonyl compounds have been a practical tool towards the synthesisof different useful heterocyclic compounds. Despite the numerous reactions with carbon-carbon double bond conjugatedcarbonyls, reactions of acetylenic carbonyls are limited. In this study, efficient dioxole synthesis was carried outvia acetylenic aldehydes and butadiene formation was preferred over cyclopropene formation via acetylenic esters asdifferent functional groups on these substrates change the product distribution. Both reaction conditions (such assolvent and temperature) and electrophilic structure of metal carbenoids alter the product distribution; acceptor (A),donor-acceptor (DA), and acceptor-acceptor (AA) functionalized diazo compounds yield different product types overdifferent mechanisms.