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
收藏
页码：1453 / 1463
页数：11
相关论文
共 50 条
  • [1] THE GENERATION AND REARRANGEMENT OF 2-DIAZOCARBONYL CYCLOBUTANONES - THE FORMATION OF 5-SPIROCYCLOPROPYL-2 (5H) FURANONES
    MILLER, RD
    THEIS, W
    HEILIG, G
    KIRCHMEYER, S
    STRAIN AND ITS IMPLICATIONS IN ORGANIC CHEMISTRY: ORGANIC STRESS AND REACTIVITY, 1989, 273 : 255 - 258
  • [2] A NOVEL REARRANGEMENT OF 2(5H)-FURANONES
    MACK, RA
    DECORY, TR
    STGEORGIEV, V
    HELVETICA CHIMICA ACTA, 1988, 71 (04) : 783 - 787
  • [3] The chemistry of 2(5H)-furanones
    Hashem, A
    Kleinpeter, E
    ADVANCES IN HETEROCYCLIC CHEMISTRY, VOL 81, 2001, 81 : 107 - 165
  • [4] PHOTOCHEMISTRY OF 2(3H)-FURANONES AND 2(5H)-FURANONES
    FILLOL, L
    MIRANDA, MA
    MORERA, IM
    SHEIKH, H
    HETEROCYCLES, 1990, 31 (04) : 751 - 782
  • [5] SYNTHESIS OF 5-ALKYL-4-BROMO-5-HYDROXY-2(5H)-FURANONES AND 5-ALKYLIDENE-4-BROMO-2(5H)-FURANONES
    FONT, J
    GRACIA, A
    DEMARCH, P
    TETRAHEDRON LETTERS, 1990, 31 (38) : 5517 - 5520
  • [6] BUTENOL SYNTHESES .3. CONVENIENT SYNTHESIS OF 5-ALKYLIDENE-2(5H)-FURANONES, 2(5H)-FURANONES AND 2-ETHOXYFURANS
    SAALFRANK, RW
    HAFNER, W
    MARKMANN, J
    BESTMANN, HJ
    TETRAHEDRON, 1988, 44 (16) : 5095 - 5100
  • [7] 2(3H)-FURANONES AND 2(5H)-FURANONES .4. THE DI-PI-METHANE REARRANGEMENT OF 3,4-BIS(PHENYLMETHYL)-2(5H)-FURANONE
    MOMOSE, T
    TANABE, G
    TSUJIMORI, H
    MURAOKA, O
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1992, 40 (09) : 2525 - 2530
  • [8] SOLVENT CONTROL OF MIGRATORY APTITUDES IN PHOTOCHEMICAL-REARRANGEMENT OF 2(5H)-FURANONES
    PADWA, A
    BROOKHART, T
    DEHM, D
    WEST, G
    WUBBELS, G
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (07) : 2347 - 2348
  • [9] NEW METHODS FOR THE SYNTHESIS OF 3(2H)-FURANONES AND 2(5H)-FURANONES
    SAIMOTO, H
    SHINODA, M
    MATSUBARA, S
    OSHIMA, K
    HIYAMA, T
    NOZAKI, H
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1983, 56 (10) : 3088 - 3092
  • [10] NEW METHODS FOR THE SYNTHESIS OF 3(2H)-FURANONES AND 2(5H)-FURANONES
    SAIMOTO, H
    MATSUBARA, S
    OSHIMA, K
    HIYAMA, T
    NOZAKI, H
    HETEROCYCLES, 1984, 21 : 600 - 600
12345