ISSN:
0009-2940
Keywords:
syn-Azo azides
;
Triaziridines, cis,cis-trialkyl-
;
Stabilization, kinetic
;
Ring expansion
;
Calculations, MMX
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The as yet unknown route to triaziridines by the addition of nitrenes to the π side of the N=N bond is achieved intramolecularly by the photolysis (thermolysis) of syn-azo azide substrates with high proximity; the yields reflect the sterical (and possibly inductive) influences of the skeleton. The product composition is rather independent of the exciting light; intramolecular azo → azide energy transfer is assumed. The kinetic skeleton stabilization of the triaziridines permits the synthesis of 17 (18) by the thermolysis of 7 (8) at 200°C with the product composition deviating only marginally from that of the photolysis. Attempts towards enlargement of the triaziridines to N3X rings (X=CHR, O, NR) lead exclusively to products of intramolecular fragmentation.
Additional Material:
3 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19911240330
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