RING-OPENING ADDITION-REACTION OF CYCLOPROPANOL DERIVATIVES WITH CARBENES

被引：5

作者：

OKU, A

IWAMOTO, M

SANADA, K

ABE, M

机构：

[1] Department of Chemistry, Materials Technology Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 47期

关键词：

D O I：

10.1016/S0040-4039(00)60864-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chloro(phenyl)carbene and diphenylcarbene reacted with cyclopropanone hemiacetals, cyclopropanols, and cyclopropanone cyanohydrins to give 4-phenylbutanoic acid derivatives. The mechanism was explained in terms of a homolytic process that the O-H group of cyclopropanols reacted as a formal H donor with carbenes.

引用

页码：7169 / 7172

页数：4

共 13 条

[1] AOKI, 1988, J AM CHEM SOC, V110, P3269
[2] INTERMEDIATES IN DECOMPOSITION OF ALIPHATIC DIAZO-COMPOUNDS .8. MECHANISM OF ETHER FORMATION FROM DIARYLMETHYLENES AND ALCOHOLS
BETHELL, D
NEWALL, AR
WHITTAKER, D
[J]. JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1971, (01): : 23 - +
[3] CYCLOPROPANOL CHEMISTRY
GIBSON, DH
DEPUY, CH
[J]. CHEMICAL REVIEWS, 1974, 74 (06) : 605 - 623
[4] KIRMSE W, 1963, LIEBIGS ANN CHEM, V666, P9
[5] CARBENES AND THE O-H BOND - SPECTROSCOPIC EVIDENCE FOR PROTONATION OF DIARYLCARBENES TO GIVE DIARYLCARBENIUM IONS
KIRMSE, W
KILIAN, J
STEENKEN, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (17) : 6399 - 6400
[6] KIRMSE W, 1971, CARBENE CHEM, P422
[7] SUBSTITUTED ACRYLONITRILES .9. REACTION OF 2-SUBSTITUTED ACRYLONITRILES WITH DIAZOALKANES - PREPARATION OF CYCLOPROPANONE CYANOHYDRINS
OKU, A
YOKOYAMA, T
HARADA, T
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (26) : 5333 - 5337
[8] OKU A, 1983, TETRAHEDRON LETT, V24, P4677
[9] AN IMPROVED SYNTHESIS OF SUBSTITUTED CYCLOPROPANONE ACETALS AND HEMIACETALS
ROUSSEAU, G
SLOUGUI, N
[J]. TETRAHEDRON LETTERS, 1983, 24 (12) : 1251 - 1254
[10] CYCLOPROPANONE HEMIACETALS
SALAUN, J
[J]. CHEMICAL REVIEWS, 1983, 83 (06) : 619 - 632

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