Carbenes and Carbene-Like Behavior in Organic Reactions
SU Ying-Peng1**, JIA Xiao-Dong2**, ZHAO Xiao-Long1
1. College of Chemistry and Chemical Engineering,Northwest Normal University,Lanzhou 730070,China; 2. School of Chemistry and Chemical Engineering,Yangzhou University,Yangzhou 225002,China
Abstract Carbenes,neutral divalent carbon reactive intermediates,are crucial in organic synthesis.Many foundational reactions taught in basic organic chemistry proceed via carbene intermediates.However,the insufficient elaboration and inadequate discussion of relevant contents often lead students to adopt a “structure change oriented” learning approach,which in turn creates considerable obstacles to their comprehension and mastery of the corresponding knowledges.This paper aims to summarize and discuss the classic “carbene-like” reaction behaviors of reagents,such as peroxyacids,carbon monoxide,isonitriles,and sulfur dioxide,based on their structures and generations.It reveals the inherent principles for governing the reaction behaviors of these carbene-like species,termed as “anions with leaving groups”.This paper aims to help students establish the logical thinking of “electronic structure determines chemical properties”,thereby enhancing their understanding and mastery of reaction mechanisms,generalize the inherently similar reaction essences of diverse structures,and ultimately improve their ability to apply theoretical knowledge and conduct scientific research innovation.
SU Ying-Peng, JIA Xiao-Dong, ZHAO Xiao-Long. Carbenes and Carbene-Like Behavior in Organic Reactions[J]. Chinese Journal of Chemical Education, 2026, 47(16): 115-125.
