99355-95-0Relevant academic research and scientific papers
Synthesis of Vinylcyclopropanes from Epoxides
Schaumann, Ernst,Kirschning, Andreas,Narjes, Frank
, p. 717 - 723 (2007/10/02)
Ring-opening of epoxides 1 by heteroatom-substituted allyl anions 2 occurs with high regioselectivity.In situ tosylation of the resulting alkoxides 3 or tosylation of the corresponding alcohols 4 yields 4-pentenyl tosylates 5.Anion generation by deprotona
copper(I) Species: Versatile Reagents To Prepare Functionally Substituted Allylic Silanes
Kleijn, Henk,Vermeer, Peter
, p. 5143 - 5148 (2007/10/02)
Smooth SN2' reactions in α-alkynyl and -allenyl oxiranes, in esters derived from α-allenic alcohols, and in the bis(methanesulfonate) derived from 1,4-dihydroxy-2-butyne were observed with the reagent copper(I).In this way, several allylic silanes bearing functional groups became available.Another route to functionally substituted allylic silanes was elaborated by adding copper(I) or its homocuprate derivative to alkynes such as 2-alkynoic esters, ethoxyacetylene, 1-alkynyl sulfides, and 1-alkynyl sulfones.The addition reactions appeared to occur regiospecifically and in many cases also with high stereoselectivity.A 1,4-bis-substituted butatriene derivative could be obtained by sequential addition of the biscuprate compound and methyl iodide to a 1-alkynyl sulfide.For one case it was shown that the addition of copper(I) to 1-alkynyl sulfones can be used to prepare sulfur-free 1-alkenes bearing in the β-position the (trimethylsilyl)methyl group.
