The elimination-addition mechanism of nucleophilic substitution at an alkylphosphonyl centre: stereospecificity, non-stereospecificity and the alkylidineoxophosphorane (phosphene) intermediate

Authors
Harger, MJP Jones, DK
Citation
Mjp. Harger et Dk. Jones, The elimination-addition mechanism of nucleophilic substitution at an alkylphosphonyl centre: stereospecificity, non-stereospecificity and the alkylidineoxophosphorane (phosphene) intermediate, CHEM COMMUN, (4), 1999, pp. 339-340
Citations number
19
Categorie Soggetti
Chemistry
Journal title
CHEMICAL COMMUNICATIONS
ISSN journal
13597345 → ACNP
Issue
4
Year of publication
1999
Pages
339 - 340
Database
ISI
SICI code
1359-7345(19990221):4<339:TEMONS>2.0.ZU;2-H
Abstract
The substitution reactions of R-2'CHP(O)(NMeR*)Cl (R-2'CH = fluoren-9-yl; R * = CHMePh) with secondary amines (Me2NH, Et2NH, (PrNHEt)-N-i) are largely stereospecific or non-stereospecific depending on the bulk of the amine and its concentration; two elimination-additon pathways, differing in whether or not the phosphene intermediate R-2'C=P(O)NMeR* becomes liberated, may be responsible.