THE GENERATION AND REARRANGEMENT OF 2-(DIAZOACETYL)CYCLOBUTANONES - THE FORMATION OF 5-SPIROCYCLOPROPYL-2(5H)-FURANONES

被引：23

作者：

MILLER, RD

THEIS, W

HEILIG, G

KIRCHMEYER, S

机构：

[1] IBM Research Division, Almaden Research Center, San Jose, California 95120-6099

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 04期

关键词：

D O I：

10.1021/jo00004a022

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe here a simple synthesis of 2-(diazoacetyl)cyclobutanones and their facile thermal rearrangement to 5-spirocyclopropyl-DELTA-alpha,beta-butenolides. The yield of the rearrangement product is high, and the reaction is completely stereospecific. alpha-Ketenylcyclobutanones have been identified spectroscopically as intermediates, and their rearrangement was studied kinetically. A strained dipolar cyclic transition is proposed for the rearrangement of the alpha-ketenylcyclobutanones to the corresponding 5-spirocyclopropyl-DELTA-alpha,beta-butenolides.

引用

页码：1453 / 1463

页数：11

共 50 条

[31] NEW SYNTHESIS OF 3-ARYL-5-ARYLMETHYLENE-2(5H)-FURANONES
RAO, YS
SYNTHETIC COMMUNICATIONS, 1976, 6 (08) : 527 - 531
[32] NEW, CONVENIENT SYNTHESIS OF 5,5-DIALKYL-2(5H)-FURANONES
GRANDGUILLOT, JC
ROUESSAC, F
SYNTHESIS-STUTTGART, 1979, (08): : 607 - 609
[33] Facile approach to 4-substituted 2(5H)-furanones
Yao, ML
Deng, MZ
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (16): : 5034 - 5036
[34] THE BROMINATION OF BETA-ANGELICA LACTONE REVISITED - SYNTHESIS OF NEW 3-BROMO-5-METHYLENE-2(5H)-FURANONES AND 3-BROMO-5-METHYL-2(5H)-FURANONES
DEECHAGUEN, CO
ORTUNO, RM
TETRAHEDRON, 1994, 50 (43) : 12457 - 12462
[35] SYNTHESIS OF 3,4-DIARYL-2(5H)-FURANONES
VIJAYARAGHAVAN, ST
BALASUBRAMANIAN, TR
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1986, 25 (07): : 760 - 761
[36] DIANION OF 2-(METHYLTHIO)-4-PENTENOIC ACID - A USEFUL REAGENT FOR THE PREPARATION OF 5-METHYLENE-2(5H)-FURANONES
TANAKA, K
TERAUCHI, M
KAJI, A
CHEMISTRY LETTERS, 1982, (03) : 351 - 352
[37] Study of structure and reactivity of spirobi-2(5H)-furanones
Jakubcova, M
Vegh, D
Lesko, J
Mastihuba, V
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1995, 60 (12) : 2119 - 2126
[38] PREPARATION OF 2(5H)-FURANONES AND DYES DERIVED FROM THEM
FORD, JA
WILSON, CV
YOUNG, WR
JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (01): : 173 - &
[39] Study of Structure and Reactivity of Spirobi-2(5H)-furanones
1600, (60):
[40] Cytotoxicity of 3,4-dihalogenated 2(5H)-furanones
Lattmann, E
Kinchington, D
Dunn, S
Singh, H
Ayuko, WO
Tisdale, MJ
JOURNAL OF PHARMACY AND PHARMACOLOGY, 2004, 56 (09) : 1163 - 1170

← 1 2 3 4 5 →