140456-06-0Relevant academic research and scientific papers
STEREOCHEMISTRY AND MECHANISM OF CYCLOPROPENE RING OPENING IN REACTIONS OF CYCLOPROPENE COMPOUNDS WITH ELECTROPHILES. STEREOCHEMISTRY OF ADDITION OF 2,4-DINITROBENZENESULFENYL CHLORIDE TO 1-METHYLCYCLOPROPENE
Kartashov, V. R.,Skorobogatova, E. V.,Afanas'ev, P. S.,Chertkov, V. A.,Sergeev, N. M.,et al.
, p. 1639 - 1648 (2007/10/02)
Cyclopropene ring opening in reactions of 1-methylcyclopropene with electrophilic reagents can be proceed with high stereoselectivity.The configuration of the products depends on the nature of the electrophile.Reaction with deuterium chloride gave products with the Z-configuration.In the reaction of 1-methylcyclopropene with reagents that tend to form cyclic intermediates (sulfenyl halides, N-bromosuccinimide, tert-butyl hypochlorite), the cyclopropene ring opened E-stereoselectively.Reaction with bromide gave a mixture of E- and Z- isomers in the ratio 3 : 1.It was established by X-ray structure analysis that 1-methylcyclopropene reacts with 2,4-dinitrobenzenesulfenyl chloride by a Markovnikov trans-addition scheme.Mechanism for the reaction of cyclopropene compounds with electrophiles are proposed and discussed.
