LEWIS ACID-PROMOTED SELECTIVE REARRANGEMENT OF TRISUBSTITUTED EPOXIDES TO ALDEHYDES OR KETONES

被引：88

作者：

MARUOKA, K ^{[1
]}

MURASE, N ^{[1
]}

BUREAU, R ^{[1
]}

OOI, T ^{[1
]}

YAMAMOTO, H ^{[1
]}

机构：

[1] NAGOYA UNIV,SCH ENGN,CHIKUSA KU,NAGOYA 46401,JAPAN

来源：

TETRAHEDRON | 1994年 / 50卷 / 12期

关键词：

D O I：

10.1016/S0040-4020(01)90389-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Rearrangement of trisubstituted epoxides has been effected under the influence of various Lewis acids. Among these, methylaluminum bis(4-bromo-2,6-di-tert-butylphenoxide) (MABR) can be selectively rearranged from trisubstituted epoxides to aldehydes, while antimony pentafluoride is employable for selective rearrangement to ketones under mild conditions.

引用

页码：3663 / 3672

页数：10

共 45 条

[1]

ARITA K, 1979, CHEM LETT, P1017

[2]

BAHRENS CH, 1983, ALDRICHIM ACTA, V16, P67

[3] NEW METHODS FOR PREPARATION OF 1-PHENYL-TRANS-CYCLOHEXANE-1,2-DIOL [J].

BERTI, G ;

BOTTARI, F ;

MACCHIA, B ;

MACCHIA, F .

TETRAHEDRON, 1965, 21 (12) :3277-&

[4] EPOXIDES OF LANOSTEROL AND SOME RELATED COMPOUNDS [J].

BOAR, RB ;

MCGHIE, JF ;

LEWIS, DA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1972, (17) :2231-+

[5] DEGRADATION OF LANOSTEROL SIDE-CHAIN [J].

BRIGGS, LH ;

BARTLEY, JP ;

RUTLEDGE, PS .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (08) :806-809

[6]

DOYLE MP, 1979, TETRAHEDRON LETT, P4429

[7] 9-THIABICYCLO[4.2.1]NONA-2,4,7-TRIENE9,9-DIOXIDE [J].

GASTEIGE.J ;

HUISGEN, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (18) :6541-+

[8]

HOGEVEEN H, 1975, TETRAHEDRON LETT, P1795

[9] THE ACID-CATALYZED REARRANGEMENT OF THE STILBENE OXIDES [J].

HOUSE, HO .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (11) :3070-3075

[10] REACTION OF RANEY-NICKEL WITH ALCOHOLS [J].

KRAFFT, ME ;

CROOKS, WJ ;

ZORC, B ;

MILCZANOWSKI, SE .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (14) :3158-3163

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