Sigmatropic [2,3]-Wittig rearrangement of alpha-allylic-heterosubstituted methylphosphonates .2. Rearrangement in the nitrogen series

被引：18

作者：

GuleaPurcarescu, M

AboutJaudet, E

Collignon, N

Saquet, M

Masson, S

机构：

[1] IRCOF,INSA,LAB HETEROCHIM ORGAN,F-76131 MONT ST AIGNAN,FRANCE

[2] UNIV CAEN,LAB CHIM MOLEC & THIOORGAN,URA 480,F-14050 CAEN,FRANCE

[3] ISMRA UNIV,F-14050 CAEN,FRANCE

来源：

TETRAHEDRON | 1996年 / 52卷 / 06期

关键词：

D O I：

10.1016/0040-4020(95)01045-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Whereas the lithiated carbanion derived from the diethyl (N-allyl, N-phenyl)-amino methylphosphonate 1 failed to undergo the [2,3]-Wittig shift, ammonium salts resulting from the quaternization of diisopropyl (N,N-diethyl)-aminomethylphosphonate 8 with allylic bromides, were conveniently rearranged into the alpha-(N,N-diethylamino)-alkenylphosphonates 11, in the presence of t-BuOK, in DMF, at -40 degrees C.

引用

页码：2075 / 2086

页数：12

共 27 条

[1]

BROEKHOF J, 1989, RECL TRAV CHIM PAY B, V108, P441

[2] REDUCTIVE LITHIATION MEDIATED ANIONIC CYCLIZATIONS AND [2,3]-SIGMATROPIC REARRANGEMENTS [J].