SIGMATROPIC [2,3]-WITTIG REARRANGEMENT OF ALPHA-ALLYLIC-HETEROSUBSTITUTED METHYLPHOSPHONATES .2. REARRANGEMENT IN THE NITROGEN SERIES

Authors
GULEAPURCARESCU M ABOUTJAUDET E COLLIGNON N SAQUET M MASSON S
Citation
M. Guleapurcarescu et al., SIGMATROPIC [2,3]-WITTIG REARRANGEMENT OF ALPHA-ALLYLIC-HETEROSUBSTITUTED METHYLPHOSPHONATES .2. REARRANGEMENT IN THE NITROGEN SERIES, Tetrahedron, 52(6), 1996, pp. 2075-2086
Citations number
27
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
52
Issue
6
Year of publication
1996
Pages
2075 - 2086
Database
ISI
SICI code
0040-4020(1996)52:6<2075:S[ROA>2.0.ZU;2-G
Abstract
Whereas the lithiated carbanion derived from the diethyl (N-allyl, N-p henyl)-amino methylphosphonate 1 failed to undergo the [2,3]-Wittig sh ift, ammonium salts resulting from the quaternization of diisopropyl ( N,N-diethyl)-aminomethylphosphonate 8 with allylic bromides, were conv eniently rearranged into the alpha-(N,N-diethylamino)-alkenylphosphona tes 11, in the presence of t-BuOK, in DMF, at -40 degrees C.