A FACILE CONVERSION OF SUBSTITUTED CYCLOBUTANONES TO CYCLOPENTANONES BY CH2I2/SMI2 SYSTEM

被引：6

作者：

FUKUZAWA, S

TSUCHIMOTO, T

机构：

[1] Department of Applied Chemistry, Chuo University, Bunkyo-ku, Tokyo

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 33期

关键词：

D O I：

10.1016/00404-0399(50)1199R-

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ring expansion reaction of a substituted cyclobutanone with CH2I2 and SmI2 proceeded cleanly in extended reaction time (15 h) to afford the corresponding cyclopentanone in good yield, whereas short reaction time (0.5 h) produced a mixture of iodohydrin and cyclopentanone.

引用

页码：5937 / 5938

页数：2

共 10 条

[1] RING EXPANSION OF CYCLOBUTANONES TO CYCLOPENTANONES VIA ALPHA-LITHIOALKYL ARYL SULFOXIDES AND SELENOXIDES
GADWOOD, RC
MALLICK, IM
DEWINTER, AJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (05) : 774 - 782
[2] VERSATILE 3-CARBON ANNELATION - SYNTHESIS OF CYCLOPENTANONES AND CYCLOPENTANONE DERIVATIVES FROM OLEFINS
GREENE, AE
DEPRES, JP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (14) : 4003 - 4005
[3] EFFICIENT REGIOSELECTIVE SYNTHESES OF ALPHA-CUPARENONES AND BETA-CUPARENONES - A NEW APPROACH FOR THE CONSTRUCTION OF THE CYCLOPENTANE RING
HALAZY, S
ZUTTERMAN, F
KRIEF, A
[J]. TETRAHEDRON LETTERS, 1982, 23 (42) : 4385 - 4388
[4] REACTIONS OF CARBONYL-COMPOUNDS WITH BENZYL CHLOROMETHYL ETHER OF DIIODOMETHANE IN THE PRESENCE OF SAMARIUM(II) IODIDE OR METALLIC SAMARIUM - NEW ROUTES TO 1,2-DIOLS, IODOHYDRINS AND CYCLOPROPANOLS
IMAMOTO, T
HATAJIMA, T
TAKIYAMA, N
TAKEYAMA, T
KAMIYA, Y
YOSHIZAWA, T
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (12): : 3127 - 3135
[5] THE REACTION OF CARBONYL-COMPOUNDS WITH DIIODOMETHANE IN THE PRESENCE OF SAMARIUM - NOVEL SYNTHESES OF IODOHYDRINS AND CYCLOPROPANOLS
IMAMOTO, T
TAKEYAMA, T
KOTO, H
[J]. TETRAHEDRON LETTERS, 1986, 27 (28) : 3243 - 3246
[6] CYCLOADDITIONS .24. IMPROVED PROCEDURE FOR ADDITION OF DICHLOROKETENE TO UNREACTIVE OLEFINS
KREPSKI, LR
HASSNER, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (14) : 2879 - 2882
[7] SYNTHESES OF SOME BICYCLO [3.3.0] OCTANE DERIVATIVES
ROBERTS, JD
GORHAM, WF
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (09) : 2278 - 2282
[8] SMI2-INDUCED IODOMETHYLATION OF CARBONYL-COMPOUNDS
TABUCHI, T
INANAGA, J
YAMAGUCHI, M
[J]. TETRAHEDRON LETTERS, 1986, 27 (33) : 3891 - 3894
[9] FACILE RING ENLARGEMENT REACTION VIA BETA-OXIDO CARBENOID
TAGUCHI, H
YAMAMOTO, H
NOZAKI, H
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1977, 50 (06) : 1592 - 1595
[10] TOTAL SYNTHESIS OF D,L-FULVINE AND D,L-CRISPATINE
VEDEJS, E
LARSEN, SD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (10) : 3030 - 3032

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