… substitution reactions of benzyl-and diphenylmethyl-phosphonamidic chlorides with amines: competition between the usual SN 2 (P) mechanism and elimination– …
MJP Harger
Index: Harger, Martin J. P. Journal of the Chemical Society, Perkin Transactions 2, 2001 , # 1 p. 41 - 47
Full Text: HTML
Citation Number: 0
Abstract
The substitution reaction of PhCH2P (O)(NMe2) Cl with Me2NH or Et2NH in CHCl3 is very sensitive to the bulk of the nucleophile (200 times slower with Et2NH), affords only the product derived from Me2NH in competition experiments, and gives largely undeuterated product with Et2ND; these features are in accord with an SN2 (P) mechanism. The corresponding reaction of Ph2CHP (O)(NMe2) Cl is relatively insensitive to the bulk of the ...
Related Articles:
[Jensen; Noller Journal of the American Chemical Society, 1949 , vol. 71, p. 2384]
[Poshkus,A.C.; Herweh,J.E. Journal of Organic Chemistry, 1964 , vol. 29, p. 2567 - 2571]
Benzylphosphonic acid inhibitors of human prostatic acid phosphatase
[Schwender; Beers; Malloy; Cinicola; Wustrow; Demarest; Jordan Bioorganic and Medicinal Chemistry Letters, 1996 , vol. 6, # 3 p. 311 - 314]
[Jensen; Noller Journal of the American Chemical Society, 1949 , vol. 71, p. 2384]