Thermal decomposition of geminal diazidomalonic acid derivatives. An intermolecular process

RM Moriarty, BR Bailey III, I Prakash

Index: Moriarty, Robert M.; Bailey , B. R.; Prakash, Indra; Miller, R. S. Journal of Organic Chemistry, 1985 , vol. 50, # 20 p. 3710 - 3713

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Citation Number: 8

Abstract

Thermal decomposition of a 1: l mixture of (CH, OCO), C (N,), and (CD, OCO), C (N,), to yield l-methyl-5-carbomethoxytetrazole-d, proceeds with crossover of the isotope label, indicating an intermolecular pathway for this reaction. A chain mechanism involving tetrazolium nucleophiles is proposed. The thermal decomposition of diazidomalonamide (14) and N, N'- dimethyldiazidomalonamide (1 6) occurs analogously yielding 5-carbamoyltetrazole (15) ...