Premium
Thermolysis of Triazoles as Melts − Is the 3,5‐Diphenyl‐1,2,4‐triazole Group a Good Leaving Group?
Author(s) -
Gautun Odd R.,
Carlsen Per H. J.
Publication year - 2000
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 - 10.1002/1099-0690(200011)2000:22<3749::aid-ejoc3749>3.0.co;2-x
Subject(s) - chemistry , moiety , thermal decomposition , alkyl , leaving group , group (periodic table) , 1,2,4 triazole , triazole , alkylation , medicinal chemistry , ion , stereochemistry , organic chemistry , catalysis
The mechanism of the rearrangement of 4‐alkyltriazoles to the corresponding 1‐alkyltriazoles on thermolysis at 330 °C is shown to involve initial formation of an intermediate 1,4‐dialkyltriazolium triazolate salt. The triazolate ion subsequently attacks at the alkyl group bearing 1‐ and 4‐positions of the dialkyltriazolium ion, yielding the observed products. No evidence for unimolecular reaction steps has been found. The triazole moiety in these compounds is only a weak leaving group, which requires activation by alkylation. Unimolecular reaction steps never take place, neither from neutral triazole species nor from activated dialkyl‐substituted triazolium species.