Synthesis of tetrahydrofurans by a tandem hydrogen atom abstraction/radical nucleophilic displacement sequence

被引：36

作者：

Crich, D

Huang, XH

Newcomb, M

机构：

[1] Univ Illinois, Dept Chem, Chicago, IL 60607 USA

[2] Wayne State Univ, Dept Chem, Detroit, MI 48202 USA

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 02期

关键词：

D O I：

10.1021/ol990564b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of a series of 5-(N-phthalimidoxy)-1-phenyl-1-(diphenylphosphatoxy)pentanes with triphenyltin hydride and AIBN provides alkoxy radicals which undergo 1,5-hydrogen atom abstraction to give beta-(phosphatoxy)alkyl radicals. These radicals then take part in a radical nucleophilic displacement leading, after chain transfer, to tetrahydrofurans.

引用

页码：225 / 227

页数：3

共 16 条

[1] On the mechanism of the tetrathiafulvalene-mediated radical-polar crossover reactions
Bashir, N
Callaghan, O
Murphy, JA
Ravishanker, T
Roome, SJ
[J]. TETRAHEDRON LETTERS, 1997, 38 (35) : 6255 - 6258
[2] Chemistry of β-(acyloxy)alkyl and β-(phosphatoxy)alkyl radicals and related species:: Radical and radical ionic migrations and fragmentations of carbon-oxygen bonds
Beckwith, ALJ
Crich, D
Duggan, PJ
Yao, QW
[J]. CHEMICAL REVIEWS, 1997, 97 (08) : 3273 - 3312
[3] A novel route to (±)-aspidospermidine:: First application of "radical-polar crossover" reactions to total synthesis
Callaghan, O
Lampard, C
Kennedy, AR
Murphy, JA
[J]. TETRAHEDRON LETTERS, 1999, 40 (01) : 161 - 164
[4] Absence of diffusively free radical cation intermediates in reactions of β-(phosphatoxy)alkyl radicals
Choi, SY
Crich, D
Horner, JH
Huang, XH
Martinez, FN
Newcomb, M
Wink, DJ
Yao, QW
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (01) : 211 - 212
[5] β-(phosphatoxy)alkyl and β-(acyloxy)alkyl radical migrations studied by laser flash photolysis
Choi, SY
Crich, D
Horner, JH
Huang, XH
Newcomb, M
Whitted, PO
[J]. TETRAHEDRON, 1999, 55 (11) : 3317 - 3326
[6] CHEMISTRY OF BETA-(PHOSPHATOXY)ALKYL AND BETA-(ACYLOXY)ALKYL RADICALS - MIGRATION REACTIONS - SCOPE AND STEREOSELECTIVITY OF BETA-(PHOSPHATOXY)ALKYL REARRANGEMENT - MECHANISM OF BETA-(PHOSPHATOXY)ALKYL AND BETA-(ACYLOXY)ALKYL MIGRATION
CRICH, D
YAO, QW
FILZEN, GF
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (46) : 11455 - 11470
[7] THE BETA-(PHOSPHONOOXY)ALKYL RADICAL REARRANGEMENT
CRICH, D
YAO, QW
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (03) : 1165 - 1166
[8] On the stereochemistry of vicinal nucleophilic substitution of β-(phosphatoxy)alkyl radicals
Crich, D
Gastaldi, S
[J]. TETRAHEDRON LETTERS, 1998, 39 (51) : 9377 - 9380
[9] CURRAN DP, 1992, SYNLETT, P943
[10] Kim S, 1998, SYNLETT, P525

← 1 2 →