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• W2061417282 endingPage "8451" @default.
• W2061417282 startingPage "8434" @default.
• W2061417282 abstract "Novel insertion reactions of dichloro- and dibromocarbene into carbon-hydrogen bonds adjacent to cyclopropane rings are reported. It is found that the predominant isomers formed in the reactions with bicyclo[4.1.0]heptane result from insertion into the endo carbon-hydrogen bonds alpha to the three-membered ring. In the reactions of bicyclo[3.1.0]hexane, however, the exo dihalocarbene insertion products are formed as the major isomers. In some compounds cyclopropane rings activate adjacent carbon-hydrogen bonds, whereas other systems containing three-membered rings do not. Moreover, the influence of various substituents (methyl, geminal dimethyl, phenyl, methoxy, and ethoxy) attached to bicyclo[3.1.0]hexane and bicyclo[4.1.0]heptane in dihalocarbene reactions has been studied. The findings can be explained by the concept of maximum orbital overlaps of Walsh orbitals of the cyclopropane rings and the alpha carbon-hydrogen bonds. In stark contrast, selective insertion into the tertiary carbon-hydrogen bonds of the cyclobutane ring in bicyclo[4.2.0]octane is observed." @default.
• W2061417282 created "2016-06-24" @default.
• W2061417282 creator A5015168231 @default.
• W2061417282 creator A5045022553 @default.
• W2061417282 creator A5079619663 @default.
• W2061417282 creator A5082169436 @default.
• W2061417282 creator A5087326466 @default.
• W2061417282 date "2007-10-01" @default.
• W2061417282 modified "2023-10-14" @default.
• W2061417282 title "Dihalocarbene Insertion Reactions into C−H Bonds of Compounds Containing Small Rings: Mechanisms and Regio- and Stereoselectivities^," @default.
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