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Hexaphenylcarbodiphosphorane (1) undergoes nucleophilic displacement reaction with halogen compounds 3 with formation of compounds 5 which can be regarded as salts of the diphosphaallylcation. 1 reacts with bromoacetic ester 11 as base, with proton abstraction and formation of a carbanion 12 which gives rise to formation of (E)-cyclopropan-tricarboxylicacid ester (13). In an analogous way, 1 attacks isothiocyanatoaceticacid ester (14) with formation of an ionpair 15 which undergoes a cycloaddition with a second molecule 14 forming 16, which can be converted into the mercaptothiazol derivative 17 by treatment with HCl.

zeitschrift für naturforschung b

Reaktionen des Hexaphenylcarbodiphosphorans, IV [1] Reaktionen des Hexaphenylcarbodiphosphorans mit Halogenverbindungen. Diphosphaallylkationen / Reactions of Hexaphenylcarbodiphosphorane, IV [1] Reactions of Hexaphenylcarbodiphosphorane with Halogen Compounds. Diphosphaallyl Cations