Abstract
The reaction of the 1,2-dioxetanes (1a-d) with the diazoalkanes (2α-η) was investigated. The two 3,3-disubstituted (3,3-dimethyl- and 3-(bro- momethyl)-3-phenyl) dioxetanes (1a and 1b), trimethyldioxetane (1c), and tetramethyldioxetane (1d) gave with the various diazoalkanes (2) the corresponding 1,3-dioxolanes (3) (insertion products) and/or the dioxetane-derived ketones (4) (fragmentation). Nucleophilic attack by the negatively charged carbon pole of the diazoalkane on the sterically less hindered site of the dioxetane peroxide bond affords the 1,3-dioxo- lane (3) after cyclization with denitrogenation of the resulting O,N dipole. The O,C dipole, formed by the nucleophilic attack of the nega- tively charged nitrogen pole on the dioxetane, is proposed as precursor to the ketones (4) through Grob-type fragmentation with regeneration of the diazoalkane
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