Diazomalonyl chloride, ethyl

Method A. Acylation of cymarin at the 4 -hydroxyl of the cymarose was performed with redistilled ethyl diazomalonyl chloride by a modi-... 

Another useful electrophilic reagent for additions to diazo compounds is bis(tri-chloromethyl) carbonate (CO(OCCl3)2 triphosgene ) As shown by Padwa s group (Marino et al., 1994 Brown et al., 1994), it allows synthesis of ethyl 2-diazomalonyl chloride (H5C2OCO - CN2 - COCl) with ethyl diazoacetate. Ethyl 2-diazomalonyl chloride can be used for the preparation of a-diazoamides (see Sect. 8.7, Schemes 8-59 and 8-66). 

The perfluoroalkanamide catalysts favor aromatic insertion over insertion or addition involving the N-substituent. The starting materials can be prepared readily from ethyl 2-diazomalonyl chloride and anilines. The oxindoles were subsequently converted to 0-trialkyl-si lyl and 0-benzoyl indoles. 

The more bulky, but more dependable, diazomalonyl group is usually introduced by the reaction of a hydroxy or amino compound with ethyl 2-diazomalonyl chloride. The treatment of cAMP with this reagent illustrates a number of points. ... 

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