ISSN:
0009-2940
Keywords:
N-Acyliminium salts, alkoxy-substituted
;
Iminium salts, N-acyl-
;
Imides
;
Alkylation
;
Azavinylogous imides
;
Amidines
;
Calculations, ab initio
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Alkylation of aliphatic imides 5 by use of oxonium salts takes place at one of the carbonyl oxygen atoms, leading to alkoxy-substituted N-acyliminium salts 1. These new reactive intermediates are fully characterized by IR, 1H- and 13C-NMR spectroscopy and X-ray analysis. The stereochemical and dynamical properties of the model compounds 6, 7 are investigated by ab initio model calculations (MP2/6-31G*//6-31G*). The barrier of rotation around the central C - N bond in 6 is calculated to 10.2 kcal/mol. The reaction with CH acids 8 yields new types of enamides (9); primary amines 10 are converted to N-acylamidines 11. Primary amidines 12 react with 1 to form new 1,3-diazabutadiene derivatives 13. The reaction with primary amides 14 gives N,N-bisacylamidines 15. With primary N-acylamidines 16 new doubly azavinylogous imides 17 (1-oxa-3,5-diazahexatriene derivatives) are formed.
Additional Material:
3 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19931260917
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