AN UNEXPECTED ACYLOIN REARRANGEMENT AND OXIDATION OF A CAMPHOR DERIVATIVE

被引：6

作者：

MCINTOSH, JM ^{[1
]}

CASSIDY, KC ^{[1
]}

机构：

[1] UNIV WINDSOR,DEPT CHEM & BIOCHEM,WINDSOR N9B 3P4,ONTARIO,CANADA

来源：

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE | 1991年 / 69卷 / 08期

关键词：

CAMPHOR; ACYLOIN REARRANGEMENT;

D O I：

10.1139/v91-195

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The trimethylsiyl ether 7 derived in two steps from camphor underwent ring expansion via an acylion rearrangement to afford two products (8 and 9) when desilylation was attempted. Compound 9 was stable but 8 was oxidized in air to homocamphoric acid anhydride 11.

引用

页码：1315 / 1319

页数：5

共 28 条

[1] BAJGROWICZ J, 1986, HETEROCYCLES, V24, P2165
[2] METAL-DIRECTED ASYMMETRIC-SYNTHESIS OF DIASTEREOISOMERIC BETA-PHENYL SERINES USING (+)-KETOPINIC ACID AS A CHIRAL AUXILIARY
CASELLA, L
JOMMI, G
MONTANARI, S
SISTI, M
[J]. TETRAHEDRON LETTERS, 1988, 29 (17) : 2067 - 2068
[3] CHAIR-BOAT CONFORMATIONAL EQUILIBRIUM IN (+)-(1S,5R)-1,8,8-TRIMETHYLBICYCLO[3.2.1]OCTAN-3-ONE
CRIST, BV
RODGERS, SL
LIGHTNER, DA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (22) : 6040 - 6045
[4] ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES
DALE, JA
DULL, DL
MOSHER, HS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) : 2543 - &
[5] DEMAYO P, 1959, MONO SESQUITERPENOID
[6] REACTIONS OF SCHIFF-BASE ANIONS WITH ELECTROPHILES - ROLE OF THE INITIAL STEREOCHEMISTRY
ELACHQAR, A
ROUMESTANT, ML
VIALLEFONT, P
[J]. TETRAHEDRON LETTERS, 1988, 29 (20) : 2441 - 2444
[7] SYNTHETIC APPLICATIONS OF TRIMETHYLSILYL CYANIDE - EFFICIENT SYNTHESIS OF BETA-AMINOMETHYL ALCOHOLS
EVANS, DA
CARROLL, GL
TRUESDALE, LK
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (07) : 914 - 917
[8] NEW CAMPHOR-DERIVED AUXILIARIES IN METHOXYSELENYLATION AND METHOXYBROMINATION WITH OPPOSITE DIASTEREOFACIAL SELECTIVITY - PREPARATION OF BETA-AMINO ALCOHOL CHIRAL SYNTHONS
ISHIZUKA, T
ISHIBUCHI, S
KUNIEDA, T
[J]. TETRAHEDRON LETTERS, 1989, 30 (26) : 3449 - 3452
[9] JACKMAN LM, 1969, APPLICATIONS NMR SPE
[10] STUDIES ON OPENING THE RINGS OF CYCLIC KETONES
JOHNSON, WS
SHELBERG, WE
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1945, 67 (10) : 1754 - 1759

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