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One‐Pot Catalytic Synthesis of gem ‐Diazides and Their Direct Conversion into Safe Materials
Author(s) -
Samuel Prinson P.,
Kundu Subrata,
Mohapatra Chandrajeet,
George Anjana,
De Susmita,
Parameswaran Pattiyil,
Roesky Herbert W.
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201700433
Subject(s) - chemistry , triflic acid , catalysis , reactivity (psychology) , azide , adduct , trimethylsilyl , organic chemistry , trimethylsilyl azide , carbene , medicine , alternative medicine , pathology
Commercial availability and storage issues have left reactivity studies of gem ‐diazides underdeveloped, in contrast to the relatively abundant chemistry of monoazides. The present study uses triflic acid (0.1 mol‐%) as a catalyst for the quantitative production of gem ‐diazides from the reaction of aldehydes with trimethylsilyl azide. The diazides could be isolated in high yields by simple evaporation of the Me 3 Si–O–SiMe 3 byproduct. In a one‐pot synthesis, the diazide was directly treated with an N‐heterocyclic carbene to obtain a gem ‐bis(triazabutadiene). Reaction of the diazide with triphenylphosphane followed by triflic acid yielded n N , N′ ‐bis(triphenylphosphane) adduct.