37828-71-0Relevant articles and documents
Electrochemical properties and reactions of organoboronic acid esters containing unsaturated bonds at their α-position
Ohtsuka, Kazuhiro,Inagi, Shinsuke,Fuchigami, Toshio
, p. G23 - G28 (2017)
Electrochemical analyses of 2-(cynnamyl)boronic acid pinacol ester and (3-phenyl-2-propynyl)boronic acid pinacol ester, and their trimethylsilyl analogues as well as their parent compounds were comparatively studied by cyclic voltammetry measurements. We
Rearrangement of alkynyl and vinyl carbenoids via the rhodium(II)-catalyzed cyclization reaction of α-diazo ketones
Padwa, Albert,Austin, David J.,Gareau, Yves,Kassir, Jamal M.,Xu, Simon L.
, p. 2637 - 2647 (2007/10/02)
o-Alkynyl-substituted α-diazoacetophenones undergo facile cyclization to indenone derivatives upon treatment with catalytic quantities of Rh(II) carboxylates. The cyclization reaction involves addition of a rhodium stabilized α-keto carbenoid onto the neighboring acetylenic π-bond to give a cyclized vinyl carbenoid. When an alkene is tethered to the alkynyl group, the vinyl carbenoid complex undergoes further cyclization to produce a cyclopropenyl-substituted indenone. Different enyl substituents resulted in a significant variation in the behavioral pattern of the reactive cyclopropene ring. The strained cyclopropene ring was intercepted with diphenylisobenzofuran to give Diels-Alder cycloadducts. For alkynyl substituted π-diazo ketones, the resulting vinyl alkynyl carbenoids were found to give products derived from an unusual alkynyl carbenoid rearrangement. The Rh(II)-catalyzed reaction of several o-dialkynyl-substituted α-diazoacetophenones which contain a group capable of undergoing reaction with the carbenoid at the terminal position was examined. Products derived from a 1,2-hydrogen shift as well as cyclopropanation of a tethered alkene was obtained in high yield. In addition, the thermal decomposition of a series of aziridinylimines derived from alkynyl-substituted aldehydes led to products derived from a rearranged alkynyl carbene. The initially formed alkynyl carbene at C1 could be induced to undergo exclusive reaction at the C3 terminal position.
