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Oxiranes exhibit two distinct ring-opening modes: cleavage of the C-O bond or cleavage of the C-C bond. Among these, reactions involving C-O bond cleavage have been extensively reviewed. This article provides an overview of the research progress over the past several decades on the cycloaddition reactions of donor-acceptor (D-A) oxiranes via C-C bond cleavage. Under suitable catalytic conditions, D-A oxiranes undergo ring-opening through C-C bond cleavage to form carbonyl ylides, which can participate in 3+n cycloaddition reactions with aldehydes, imines, alkenes, alkynes, indoles, purines, etc.
Zhang et al. (Tue,) studied this question.