Thallium trinitrate-mediated ring contraction of 1,2-dihydronaphthalenes: an approach to the synthesis of indans

被引：30

作者：

Ferraz, HMC ^{[1
]}

Silva, LF ^{[1
]}

Vieira, TO ^{[1
]}

机构：

[1] Univ Sao Paulo, Inst Quim, BR-05508900 Sao Paulo, Brazil

来源：

TETRAHEDRON | 2001年 / 57卷 / 09期

基金：

巴西圣保罗研究基金会;

关键词：

oxidation; thallium trinitrate; ring contraction; indans;

D O I：

10.1016/S0040-4020(00)01174-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Oxidation of 1,2-dihydronaphthalenes with thallium trinitrate was studied. 1,2-dihydronaphthalene, 1-methyl-1,2-dihydronaphthalene, 6- and 8-methoxy-1,2-dihydronaphthalenes gave rise to the respective ring contraction products in good yields, whereas the rearrangement was not observed using 4-methyl-1,2-dihydronaphthalene and 1-n-butyl-4-methyl-1,2-dihydronaphthalene as substrates. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：1709 / 1713

页数：5

共 31 条

[1] HYDROXYMERCURATION AND THALLIUM(III) OXIDATION OF CYCLOALKENES AND METHYLENECYCLOALKANES
ABLEY, P
BYRD, JE
HALPERN, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (08) : 2591 - 2596
[2] ANDERSON CB, 1963, J ORG CHEM, V28, P605
[3] RING CONTRACTION OF 2,2-DIMETHYL-2H-CHROMENES BY OXIDATION WITH THALLIUM(III) NITRATE - SYNTHESIS OF CORYLIN
ANTUS, S
GOTTSEGEN, A
NOGRADI, M
GERGELY, A
[J]. CHEMISCHE BERICHTE-RECUEIL, 1979, 112 (12): : 3879 - 3885
[4] THE STEREOCHEMISTRY OF RING-CLOSURE OF SOME MONOSUBSTITUTED ORTHO-(BUT-3-ENYL)PHENYL RADICALS
BECKWITH, ALJ
GERBA, S
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1992, 45 (01) : 289 - 308
[5] THALLIUM(III) NITRATE OXIDATION OF CHROMENS - CIS-DIHYDROXYLATION AND DIALKOXYLATION
BEGLEY, MJ
MOHAMED, SE
WHITING, DA
DSOUZA, F
HATAM, NAR
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (04): : 883 - 887
[6] BILKIS II, 1994, J ORG CHEM, V30, P951
[7] NATURAL TERPENE DERIVATIVES .88. COMPONENTS OF TRIBE MUTISIEAE
BOHLMANN, F
ZDERO, C
[J]. PHYTOCHEMISTRY, 1977, 16 (02) : 239 - 242
[8] NATURAL TERPENE DERIVATIVES .168. NEW GERANYLCOUMARIN DERIVATIVES AND OTHER COMPOUNDS FROM THE TRIBE MUTISIEAE
BOHLMANN, F
ZDERO, C
LEVAN, N
[J]. PHYTOCHEMISTRY, 1979, 18 (01) : 99 - 102
[9] CHEMISTRY OF SINGLET OXYGEN .24. LOW-TEMPERATURE PHOTOOXYGENATION OF 1,2-DIHYDRONAPHTHALENES
BURNS, PA
FOOTE, CS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (06) : 908 - 916
[10] Reaction of 3-alkenols with thallium trinitrate: An unexpected and useful ring contraction
Ferraz, HMC
Santos, AP
Silva, LF
Vieira, TD
[J]. SYNTHETIC COMMUNICATIONS, 2000, 30 (04) : 751 - 762

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