10.1016/0040-4039(91)80012-U
The research aimed to explore the reactions of carbenes with bicyclo[1.1.0]butanes, particularly focusing on tricyclo[4.1.0]heptane (1). The study sought to propose a new mechanism for these reactions, specifically regarding the opening of side bonds rather than central bonds. The researchers found that the reactions predominantly led to the opening of side bonds, with the formation of various products such as 21, endo-6-endo-7-dibromobicyclo[3.1.1]heptane (3), and other isomers. The study concluded that electrophilic attacks on bicyclo[1.1.0]butanes preferentially occur at the bridgehead carbons, leading to the opening of strained side bonds rather than the central bond. This finding challenges previous mechanisms and provides new insights into the behavior of carbenes in such reactions.