Diazoalkanes multiple bond reactions

Tnfluoromethyldiazomethane behaves as atypical diazoalkane in its additions to carbon-carbon multiple bonds [9] For example, its reactions with ethylene and... 

Alkylidene sulfenes (75), generally prepared by the dehydrohalogenation of alkylsulfonyl chlorides, add readily to electron-rich multiple bonds. For example, with enamines, the thietane dioxide (e.g., 76) is formed diazoalkanes yield thiirane dioxides (episulfones) and imines (Schiff bases) afford 1,2-thiazetidine 1,1-dioxides. There are available numerous reviews of sulfenes, including cycloaddition reactions.102... 

The availability of phosphaalkenes R1P=CR22 and phosphaalkynes RC=P has led to the development of another route to phosphiranes and phosphirenes involving the formal addition of carbenes to phosphorus-carbon multiple bonds. When using diazoalkanes as the carbene source, the reaction mechanism involves the series of steps demonstrated by Niecke and co-workers in Scheme 23 <8iAG(E)i3i, 83CC1171) see also <75AG(E)363>. 

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