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On the reactivity of o-lithloaryl ethers:: Tandem anion translocation and Wittig rearrangement
被引:48
作者
:
Barluenga, J
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Oviedo, Inst Univ Quim Organomet Enrique Mol, Unidad Asociada, CSIC, Oviedo 33071, Spain
Barluenga, J
Fañanás, FJ
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Oviedo, Inst Univ Quim Organomet Enrique Mol, Unidad Asociada, CSIC, Oviedo 33071, Spain
Fañanás, FJ
Sanz, R
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Oviedo, Inst Univ Quim Organomet Enrique Mol, Unidad Asociada, CSIC, Oviedo 33071, Spain
Sanz, R
Marcos, C
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Oviedo, Inst Univ Quim Organomet Enrique Mol, Unidad Asociada, CSIC, Oviedo 33071, Spain
Marcos, C
Trabada, M
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Oviedo, Inst Univ Quim Organomet Enrique Mol, Unidad Asociada, CSIC, Oviedo 33071, Spain
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
收藏
页码:1587 / 1590
页数:4
相关论文
共 28 条
[1]
Dearomatising cyclisations of lithiated N-benzylbenzamides
[J].
Ahmed, A
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England
Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England
Ahmed, A
;
Clayden, J
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England
Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England
Clayden, J
;
Yasin, SA
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England
Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England
Yasin, SA
.
CHEMICAL COMMUNICATIONS,
1999,
(03)
:231
-232
[2]
Anionic cyclisations of an N-benzyl naphthamide:: a route to benzo[e]isoindolones
[J].
Ahmed, A
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England
Ahmed, A
;
Clayden, J
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England
Clayden, J
;
Rowley, M
论文数:
0
引用数:
0
h-index:
0
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Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England
Rowley, M
.
CHEMICAL COMMUNICATIONS,
1998,
(03)
:297
-298
[3]
Anion translocation in organolithiums: A mechanism for the lithiation and cyclisation of tertiary naphthamides
[J].
Ahmed, A
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England
Ahmed, A
;
Clayden, J
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引用数:
0
h-index:
0
机构:
Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England
Clayden, J
;
Rowley, M
论文数:
0
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0
h-index:
0
机构:
Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England
Rowley, M
.
TETRAHEDRON LETTERS,
1998,
39
(34)
:6103
-6106
[4]
Isomerization of 2-(2-propenoxy)phenyllithium: Tandem anionic cyclization gamma-elimination
[J].
Bailey, WF
论文数:
0
引用数:
0
h-index:
0
机构:
De La Salle University, Department of Chemistry, Manila
Bailey, WF
;
Punzalan, ER
论文数:
0
引用数:
0
h-index:
0
机构:
De La Salle University, Department of Chemistry, Manila
Punzalan, ER
.
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
[J].
Barluenga, J
论文数:
0
引用数:
0
h-index:
0
机构:
Inst. Univ. de Quim. Orgmet. E., Unidad Asociada al C.S.I.C., Universidad de Oviedo, 33071 Oviedo, Julián Clavería
Barluenga, J
;
Sanz, R
论文数:
0
引用数:
0
h-index:
0
机构:
Inst. Univ. de Quim. Orgmet. E., Unidad Asociada al C.S.I.C., Universidad de Oviedo, 33071 Oviedo, Julián Clavería
Sanz, R
;
Fananas, FJ
论文数:
0
引用数:
0
h-index:
0
机构:
Inst. Univ. de Quim. Orgmet. E., Unidad Asociada al C.S.I.C., Universidad de Oviedo, 33071 Oviedo, Julián Clavería
Fananas, FJ
.
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
[J].
EISCH, JJ
论文数:
0
引用数:
0
h-index:
0
机构:
CATHOLIC UNIV AMER, DEPT CHEM, WASHINGTON, DC 20017 USA
EISCH, JJ
;
KOVACS, CA
论文数:
0
引用数:
0
h-index:
0
机构:
CATHOLIC UNIV AMER, DEPT CHEM, WASHINGTON, DC 20017 USA
KOVACS, CA
;
RHEE, SG
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0
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0
h-index:
0
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CATHOLIC UNIV AMER, DEPT CHEM, WASHINGTON, DC 20017 USA
RHEE, SG
.
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
[J].
Fleming, I
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
Fleming, I
;
Mack, SR
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
Mack, SR
;
Clark, BP
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
Clark, BP
.
CHEMICAL COMMUNICATIONS,
1998,
(06)
:715
-716
[9]
WITTIG REARRANGEMENTS OF ARALKYL ALKYL ETHERS
[J].
GARST, JF
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV GEORGIA,DEPT CHEM,ATHENS,GA 30602
UNIV GEORGIA,DEPT CHEM,ATHENS,GA 30602
GARST, JF
;
SMITH, CD
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV GEORGIA,DEPT CHEM,ATHENS,GA 30602
UNIV GEORGIA,DEPT CHEM,ATHENS,GA 30602
SMITH, CD
.
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-
[J].
HOFFMANN, R
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV WURZBURG, INST ORGAN CHEM, HUBLAND, W-8700 WURZBURG, GERMANY
UNIV WURZBURG, INST ORGAN CHEM, HUBLAND, W-8700 WURZBURG, GERMANY
HOFFMANN, R
;
RUCKERT, T
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV WURZBURG, INST ORGAN CHEM, HUBLAND, W-8700 WURZBURG, GERMANY
UNIV WURZBURG, INST ORGAN CHEM, HUBLAND, W-8700 WURZBURG, GERMANY
RUCKERT, T
;
BRUCKNER, R
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV WURZBURG, INST ORGAN CHEM, HUBLAND, W-8700 WURZBURG, GERMANY
UNIV WURZBURG, INST ORGAN CHEM, HUBLAND, W-8700 WURZBURG, GERMANY
BRUCKNER, R
.
TETRAHEDRON LETTERS,
1993,
34
(02)
:297
-300
←
1
2
3
→
共 28 条
[1]
Dearomatising cyclisations of lithiated N-benzylbenzamides
[J].
Ahmed, A
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England
Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England
Ahmed, A
;
Clayden, J
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England
Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England
Clayden, J
;
Yasin, SA
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England
Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England
Yasin, SA
.
CHEMICAL COMMUNICATIONS,
1999,
(03)
:231
-232
[2]
Anionic cyclisations of an N-benzyl naphthamide:: a route to benzo[e]isoindolones
[J].
Ahmed, A
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England
Ahmed, A
;
Clayden, J
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England
Clayden, J
;
Rowley, M
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England
Rowley, M
.
CHEMICAL COMMUNICATIONS,
1998,
(03)
:297
-298
[3]
Anion translocation in organolithiums: A mechanism for the lithiation and cyclisation of tertiary naphthamides
[J].
Ahmed, A
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England
Ahmed, A
;
Clayden, J
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England
Clayden, J
;
Rowley, M
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England
Rowley, M
.
TETRAHEDRON LETTERS,
1998,
39
(34)
:6103
-6106
[4]
Isomerization of 2-(2-propenoxy)phenyllithium: Tandem anionic cyclization gamma-elimination
[J].
Bailey, WF
论文数:
0
引用数:
0
h-index:
0
机构:
De La Salle University, Department of Chemistry, Manila
Bailey, WF
;
Punzalan, ER
论文数:
0
引用数:
0
h-index:
0
机构:
De La Salle University, Department of Chemistry, Manila
Punzalan, ER
.
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
[J].
Barluenga, J
论文数:
0
引用数:
0
h-index:
0
机构:
Inst. Univ. de Quim. Orgmet. E., Unidad Asociada al C.S.I.C., Universidad de Oviedo, 33071 Oviedo, Julián Clavería
Barluenga, J
;
Sanz, R
论文数:
0
引用数:
0
h-index:
0
机构:
Inst. Univ. de Quim. Orgmet. E., Unidad Asociada al C.S.I.C., Universidad de Oviedo, 33071 Oviedo, Julián Clavería
Sanz, R
;
Fananas, FJ
论文数:
0
引用数:
0
h-index:
0
机构:
Inst. Univ. de Quim. Orgmet. E., Unidad Asociada al C.S.I.C., Universidad de Oviedo, 33071 Oviedo, Julián Clavería
Fananas, FJ
.
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
[J].
EISCH, JJ
论文数:
0
引用数:
0
h-index:
0
机构:
CATHOLIC UNIV AMER, DEPT CHEM, WASHINGTON, DC 20017 USA
EISCH, JJ
;
KOVACS, CA
论文数:
0
引用数:
0
h-index:
0
机构:
CATHOLIC UNIV AMER, DEPT CHEM, WASHINGTON, DC 20017 USA
KOVACS, CA
;
RHEE, SG
论文数:
0
引用数:
0
h-index:
0
机构:
CATHOLIC UNIV AMER, DEPT CHEM, WASHINGTON, DC 20017 USA
RHEE, SG
.
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
[J].
Fleming, I
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
Fleming, I
;
Mack, SR
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
Mack, SR
;
Clark, BP
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
Clark, BP
.
CHEMICAL COMMUNICATIONS,
1998,
(06)
:715
-716
[9]
WITTIG REARRANGEMENTS OF ARALKYL ALKYL ETHERS
[J].
GARST, JF
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV GEORGIA,DEPT CHEM,ATHENS,GA 30602
UNIV GEORGIA,DEPT CHEM,ATHENS,GA 30602
GARST, JF
;
SMITH, CD
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV GEORGIA,DEPT CHEM,ATHENS,GA 30602
UNIV GEORGIA,DEPT CHEM,ATHENS,GA 30602
SMITH, CD
.
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-
[J].
HOFFMANN, R
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV WURZBURG, INST ORGAN CHEM, HUBLAND, W-8700 WURZBURG, GERMANY
UNIV WURZBURG, INST ORGAN CHEM, HUBLAND, W-8700 WURZBURG, GERMANY
HOFFMANN, R
;
RUCKERT, T
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV WURZBURG, INST ORGAN CHEM, HUBLAND, W-8700 WURZBURG, GERMANY
UNIV WURZBURG, INST ORGAN CHEM, HUBLAND, W-8700 WURZBURG, GERMANY
RUCKERT, T
;
BRUCKNER, R
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV WURZBURG, INST ORGAN CHEM, HUBLAND, W-8700 WURZBURG, GERMANY
UNIV WURZBURG, INST ORGAN CHEM, HUBLAND, W-8700 WURZBURG, GERMANY
BRUCKNER, R
.
TETRAHEDRON LETTERS,
1993,
34
(02)
:297
-300
←
1
2
3
→