37828-71-0Relevant academic research and scientific papers
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
Silver ion-assisted solvolysis of 2,2-dibromo-1-phenylcyclopropanecarboxylic acid: Solvent-dependent competition between decarboxylation and ring closure
Sydnes, Leiv K.,Mungaroo, Rajesh,Svendsen, John S.
, p. 1392 - 1398 (2007/10/03)
The solvolysis of the title compound has been studied in several alcohols (methanol, 2,2,2-trifluoroethanol, isopropyl alcohol, tert-butyl alcohol and ,1,1,3,3,3-hcxafluoro-2-propanol [HFP]) in the presence of an excess of silver trifluoroacetale. In all solvents the corresponding butenolide, 4-bromo-3-phenyl-2(5H)-furanone, was a major or the predominant product. Another product formed in all solvents but HFP was (Z)-4-alkoxy-3-bromo-2-phenyl-2-butenoic acid, which resulted from solvent attack on intermediate allylic cations. Furthermore, both 3-alkoxy-1-phenyl-1-propyne and 3-alkoxy-1-phenyl-1-propanone were formed except when reactions were performed in HFP; their formation involved decarboxylation and their total yield was 15-40%. Acta Chemica Scandinavica 1998.
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.
A STUDY OF THE REARRANGEMENT CHEMISTRY OF ALKYNYL CARBENES
Padwa, Albert,Gareau, Yves,Xu, Simon L.
, p. 983 - 986 (2007/10/02)
Thermal decomposition of a series of aziridinylimines derived from alkynyl substituted aldehydes lead to products derived from a rearranged alkynyl carbene.
