Takashi Tsuji, Edward M. Kosower, Takashi Tsuji

Research output: Contribution to journalArticlepeer-review


A series of alkyldiazenes, RN=NH (R = CH3, CH3CH2, (CH3)2CH, (CH3)3C, (CH3)3CCH(CH3), c-C3H6, and c-C6H11), has been generated by two different routes, decarboxylation (RN=NCOO- + H+) and elimination (RN(Ts)NH2 + OC2H5-).All alkyldiazenes react rapidly with oxygen and disappear in a bimolecular process, like alkenyldiazenes and aryldiazenes.The rate of the bimolecular reaction varies from 0.015 M-1 sec-1 for cyclopropyldiazene to 4.5 M-1 sec-1 for 3,3-dimethyl-2-butyldiazene.The nmr spectrum of methyldiazene in CH3CN at —48° reveals a quadrupole-broadened band for NH at τ —5.6 ± 0.2 and a doublet for the methyl group at +6.13 (J ~ 2 Hz).The n → Π* transition energy for an alkyldiazene falls as the rate of the bimolecular reaction increases.The products of the bimolecular reaction are the corresponding hydrocarbon (RH) (the major product) and the symmetrical hydrazine (RNHNHR).The role of the alkyldiazenes as reaction intermediates is discussed.The pKa of tert-butyldiazene is estimated as 19-21.

Original languageEnglish
Pages (from-to)1992-1999
Number of pages8
JournalJournal of the American Chemical Society
Issue number8
StatePublished - 1 Apr 1971
Externally publishedYes


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