Dihalocarbenes imine reactions

REACTIONS OF DIHALOCARBENES WITH AMINES, IMINES, AMIDES AND RELATED COMPOUNDS... 

The oxidation of phenylhydrazine and 1,2-disubstituted hydrazines to hydrazones and diazenes by CI2C proceeds via formation of unstable azomethine imines.95 The conversion of alcohols into alkyl halides is achieved by reaction with CCI4 (or CBr4) in DMF under electrochemical reduction.96 The reaction of dihalocarbene X2C with DMF to form a Vilsmaier reagent (93) is proposed as the key process. The reaction of simple isocyanates (RNCO) with dimethoxycarbene normally gives hydantoin-type products. In the reaction with vinyhsocyanates such as (94), however, hydroindoles (95) are formed in good yields.97... 

The addition of carbenes and carbenoids to imines and nitriles continues to be a popular approach to aziridines and 2//-azirines. These processes have been well reviewed by Deyrup (B-83MI101-01). Dichlorocarbene and other dihalocarbenes have been added to a wide variety of imines to provide dihaloaziridines. A recent example is shown in Equation (64), illustrating the use of phase-transfer conditions <93H(36)69i). The treatment of azides with excess dichlorocarbene results in the formation of the 2,2,3,3-tetrachloroaziridines (92TL2339). Presumably, the azide is converted by dichlorocarbene to the imidoyl dihalide RN=CC12 which reacts further with dichlorocarbene. Transition metal-promoted reaction of a-diazoesters with imines provides 2-(alkoxycarbonyl)aziridines [Pg.46]

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