ALPHA-METHYLENE-BETA-LACTONES AS NOVEL ALLENE EQUIVALENTS - REGIOSELECTIVE [4+2]-CYCLOADDITION AND STEREOSELECTIVE DECARBOXYLATION FOR THE INTRODUCTION OF EXO-ALKYLIDENE FUNCTIONALITIES

被引：13

作者：

ADAM, W

HASEMANN, L

机构：

[1] Institute of Organic Chemistry, University of Würzburg, D-8700 Würzburg, Am Hubland

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 48期

关键词：

ALLENE EQUIVALENTS; ALPHA-METHYLENE-BETA-LACTONES; REGIOSELECTIVITY; STEREOSELECTIVITY; DECARBOXYLATION;

D O I：

10.1016/0040-4039(91)85032-Z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Beta-Lactone-capped allene dienophiles afforded with cyclopentadiene spiro-beta-lactone as [4 + 2] cycloadducts, which on thermal decarboxylation gave regio- and stereoselectively E-5-alkylidene 2-norbornenes.

引用

页码：7033 / 7036

页数：4

共 20 条

[1] ALPHA-METHYLENE BETA-S-THIOLACTONES - SYNTHESIS OF A NEW HETEROCYCLE BY SULFURIZATION OF AN ALPHA-METHYLENE BETA-LACTONE AND ITS STRUCTURE
ADAM, W
HASEMANN, L
[J]. CHEMISCHE BERICHTE, 1990, 123 (06) : 1449 - 1451
[2] STEREOSPECIFIC INTRODUCTION OF DOUBLE-BONDS VIA THERMOLYSIS OF BETA-LACTONES
ADAM, W
BAEZA, J
LIU, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (06) : 2000 - &
[3] SYNTHESIS OF ENDOPEROXIDES DERIVED FROM CYCLOOCTATETRAENES VIA SINGLET OXYGENATION
ADAM, W
KLUG, G
PETERS, EM
PETERS, K
VONSCHNERING, HG
[J]. TETRAHEDRON, 1985, 41 (11) : 2045 - 2056
[4] ADAM W, IN PRESS J ORG CHEM
[5] [Anonymous], 1988, ANGEW CHEM, V100, P1594
[6] BOUJOUKLIAN R, 1977, J ORG CHEM, V42, P4095
[7] CAMPI EM, 1990, SYNTHESIS-STUTTGART, P855
[8] CUMICO RF, 1971, ORGANOMETALL CHEM SY, V1, P253
[9] RESEARCHES ON ACETYLENIC COMPOUNDS .47. THE PROTOTROPIC REARRANGEMENTS OF SOME ACETYLENIC DICARBOXYLIC ACIDS
JONES, ERH
MANSFIELD, GH
WHITING, MC
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1954, (SEP): : 3208 - 3212
[10] SYNTHESIS AND CHEMISTRY OF 1,1-DIFLUOROALLENE
KNOTH, WH
COFFMAN, DD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (15) : 3873 - 3875

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