First N-alkyl heterolysis of tertiary benzamides in neutral conditions

Authors
Auzeil, N Tomas, A Fleury, MB Largeron, M
Citation
N. Auzeil et al., First N-alkyl heterolysis of tertiary benzamides in neutral conditions, TETRAHEDR L, 41(45), 2000, pp. 8781-8785
Citations number
19
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
45
Year of publication
2000
Pages
8781 - 8785
Database
ISI
SICI code
0040-4039(20001104)41:45<8781:FNHOTB>2.0.ZU;2-L
Abstract
Tertiary benzamides 1-4 bearing a tricyclopropylmethyl substituent were syn thesized and found to undergo rapid alkyl-nitrogen heterolysis at pH 7. X-R ay diffraction structural data for these amides revealed that their ability to give N-alkyl fission was not induced by the pyramidalization of the nit rogen atom, in contrast to what has been observed in the case of N-acyl cle avage (hydrolysis). (C) 2000 Elsevier Science Ltd. All rights reserved.