On the reactivity of o-lithloaryl ethers:: Tandem anion translocation and Wittig rearrangement

被引：48

作者：

Barluenga, J

Fañanás, FJ

Sanz, R

Marcos, C

Trabada, M

机构：

[1] Univ Oviedo, Inst Univ Quim Organomet Enrique Mol, Unidad Asociada, CSIC, Oviedo 33071, Spain

[2] Univ Burgos, Fac Ciencias, Dept Quim, Area Quim Organ, Burgos 09001, Spain

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 09期

关键词：

D O I：

10.1021/ol0258029

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Allyl and benzyl 2-lithloaryl ethers, generated by bromine-lithium exchange in THF, undergo a new tandem anion translocation-[1,2]-Wittig rearrangement allowing the isolation of the corresponding benzylic alcohols.

引用

页码：1587 / 1590

页数：4

共 28 条

[1] Dearomatising cyclisations of lithiated N-benzylbenzamides
Ahmed, A
Clayden, J
Yasin, SA
[J]. CHEMICAL COMMUNICATIONS, 1999, (03) : 231 - 232
[2] Anionic cyclisations of an N-benzyl naphthamide:: a route to benzo[e]isoindolones
Ahmed, A
Clayden, J
Rowley, M
[J]. CHEMICAL COMMUNICATIONS, 1998, (03) : 297 - 298
[3] Anion translocation in organolithiums: A mechanism for the lithiation and cyclisation of tertiary naphthamides
Ahmed, A
Clayden, J
Rowley, M
[J]. TETRAHEDRON LETTERS, 1998, 39 (34) : 6103 - 6106
[4] Isomerization of 2-(2-propenoxy)phenyllithium: Tandem anionic cyclization gamma-elimination
Bailey, WF
Punzalan, ER
[J]. TETRAHEDRON LETTERS, 1996, 37 (31) : 5435 - 5436
[5] Regio- and stereoselective copper-induced isomerization of 2-alkenyl 2-lithiophenyl ethers to 2-(2-alkenyl)phenols
Barluenga, J
Sanz, R
Fananas, FJ
[J]. TETRAHEDRON LETTERS, 1997, 38 (34) : 6103 - 6106
[6] Chaudhari SS, 1999, SYNLETT, P1763
[7] REARRANGEMENTS OF ORGANOMETALLIC COMPOUNDS .10. MECHANISM OF 1,2-ARYL MIGRATION IN WITTIG REARRANGEMENT OF ALPHA-METALLATED BENZYL ARYL ETHERS
EISCH, JJ
KOVACS, CA
RHEE, SG
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1974, 65 (03) : 289 - 301
[8] Formation of α-dialkylamino alkyllithium intermediates in the reaction of N,N-dialkylamides with PhMe2SiLi followed by a second lithium reagent, and their alkylation, fragmentation, cyclisation and rearrangement by proton transfer
Fleming, I
Mack, SR
Clark, BP
[J]. CHEMICAL COMMUNICATIONS, 1998, (06) : 715 - 716
[9] WITTIG REARRANGEMENTS OF ARALKYL ALKYL ETHERS
GARST, JF
SMITH, CD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (06) : 1526 - 1537
[10] [1,2]-WITTIG REARRANGEMENT OF A LITHIOALKYL BENZYL ETHER WITH INVERSION OF CONFIGURATION AT THE CARBANION-C ATOM - DIASTEREOSELECTIVE REDUCTIONS OF CYCLOHEXYL RADICALS WITH LI+ ARENE-
HOFFMANN, R
RUCKERT, T
BRUCKNER, R
[J]. TETRAHEDRON LETTERS, 1993, 34 (02) : 297 - 300

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