SYNTHESIS OF ALPHA-METHYLENE BETA-LACTONES, NOVEL HETEROCYCLES

被引：26

作者：

ADAM, W ^{[1
]}

ALBERT, R ^{[1
]}

GRAU, ND ^{[1
]}

HASEMANN, L ^{[1
]}

NESTLER, B ^{[1
]}

PETERS, EM ^{[1
]}

PETERS, K ^{[1
]}

PRECHTL, F ^{[1
]}

VONSCHNERING, HG ^{[1
]}

机构：

[1] MAX PLANCK INST FESTKORPERFORSCH,W-7000 STUTTGART,GERMANY

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 20期

关键词：

D O I：

10.1021/jo00020a016

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Triphenylphosphine deoxygenation of beta-alkyl, beta,beta-dialkyl-, and beta,beta-spirocycloalkyl-substituted alpha-methylene-beta-peroxy lactones 3a-k, which are readily available by photooxygenation of the corresponding alpha,beta-unsaturated carboxylic acids 1, and cyclization of the resulting alpha-methylene-beta-hydroperoxy acids 2 constitute a convenient method for the preparation of a variety of alpha-methylene beta-lactones 5. Alternatively, the alpha-methylene-beta-hydroxy carboxylic acids 4 can be directly cyclized by benzenesulfonyl chloride in pyridine into these novel four-membered ring heterocycles 5.

引用

页码：5778 / 5781

页数：4

共 22 条

[1] ON THE REACTION OF ALPHA-METHYLENE-BETA-PEROXY LACTONES WITH OLEFINS [J].

ADAM, W ;

GRIESBECK, A ;

KAPPES, D .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (23) :4479-4481

[2] ON THE MECHANISM OF THE "TRIPHENYLPHOSPHINE-AZODICARBOXYLATE (MITSUNOBU REACTION) ESTERIFICATION [J].

ADAM, W ;

NARITA, N ;

NISHIZAWA, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (06) :1843-1845

[3] ALPHA-METHYLENE BETA-S-THIOLACTONES - SYNTHESIS OF A NEW HETEROCYCLE BY SULFURIZATION OF AN ALPHA-METHYLENE BETA-LACTONE AND ITS STRUCTURE [J].

ADAM, W ;

HASEMANN, L .

CHEMISCHE BERICHTE, 1990, 123 (06) :1449-1451

[4] STEREOSPECIFIC INTRODUCTION OF DOUBLE-BONDS VIA THERMOLYSIS OF BETA-LACTONES [J].

ADAM, W ;

BAEZA, J ;

LIU, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (06) :2000-&

[5] SYNTHESIS OF ENDOPEROXIDES DERIVED FROM CYCLOOCTATETRAENES VIA SINGLET OXYGENATION [J].

ADAM, W ;

KLUG, G ;

PETERS, EM ;

PETERS, K ;

VONSCHNERING, HG .

TETRAHEDRON, 1985, 41 (11) :2045-2056

[6] TRIPHENYLPHOSPHINE DEOXYGENATION OF MALONYL PEROXIDES, A NOVEL ROUTE TO MALONYL ANHYDRIDES [J].

ADAM, W ;

DIEHL, JW .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1972, (13) :797-&

[7]

ADAM W, J ORG CHEM

[8]

Adam W., 1985, ANGEW CHEM, V97, P1071

[9]

[Anonymous], 1988, ANGEW CHEM, V100, P1594

[10] PHOSPHITE-MEDIATED IN SITU CARBOXYVINYLATION - A NEW GENERAL ACRYLIC-ACID SYNTHESIS [J].

BRITTELLI, DR .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (12) :2514-2520

← 1 2 3 →