93863-22-0Relevant academic research and scientific papers
Gold(I)-catalyzed reactions of propargyl esters with vinyl derivatives
Sperger, Christian A.,Tungen, Jorn E.,Fiksdahl, Anne
supporting information; experimental part, p. 3719 - 3722 (2011/09/12)
A gold-catalyzed olefin cyclopropanation reaction of propargyl esters with vinyl ester or vinyl sulfonamide derivatives was investigated for the synthesis of highly substituted cyclopropane derivatives in good diastereoselectivity. By varying the vinyl sp
Transition metal-catalyzed pentannulation of propargyl acetates via styrylcarbene intermediates
Nakanishi, Yusuke,Miki, Koji,Ohe, Kouichi
, p. 12138 - 12148 (2008/02/10)
The indene formation from phenyl-substituted sec- and tert-propargyl esters (terminal alkynes) was achieved by platinum or ruthenium catalysis via E-vinylcarbenoid intermediate. Considering the competitive reactions of pentannulation versus cyclopropanati
Mechanisms for Manganese(III) Osidations with Alkenes
Fristad, William E.,Peterson, John R.,Ernst, Andreas B.,Urbi, Gordon B.
, p. 3429 - 3442 (2007/10/02)
In the reaction of manganese(III) acetate with carboxylic acids and alkenes, three distinct processes have been identified which involve the alkene and two processes which are independent of alkene.A combination of product studies, rearrangements, dilution experiments and literature kinetic data allow the proposal of a unified mechanistic picture to describe these processes.Specifically, the role of α-H acidity of the carboxylyic acid component, electron deficient radical additions, metal complexed organic radicals, and the importance of an oxo-centered manganese(III) triangle are discussed as they relate to the lactone annulation reaction.Single electron transfer oxidation of alkenes is described as a route toward 1,2-diacetates of alkenes within the 8.1-7.5 eV I.P. range.Three less common modes of Mn(III) reaction are discussed and compared with the two primary processes of lactone annulation and 1,2-diacetate formation.
Manganese(III)-Mediated γ-Lactone Annulation
Fristad, William E.,Peterson, John R.
, p. 10 - 18 (2007/10/02)
The annulation of a γ-lactone ring onto an alkene by manganese(III) acetate oxidation of acetic acid was investigated.The regioselectivity of addition to unsymmetrically substituted alkenes is reported along with the stereoselectivity of addition to various acyclic and cyclic alkenes.Alkenes with ionization potentials above 8.2 eV were found to react in good yield.The role of acetic anhydride in these reactions was studied, and it was shown to be oxidized faster than acetic acid and also led to different products.The fate of oxidized acetic acid or anhydridein the absence of suitable acceptor molecule has also been quantitatively identified.The relationship of enolizability, or C-H acidity, of the carboxylic acid being oxidized was established quantitatively.
