STEREOSELECTIVE REARRANGEMENTS OF CONFORMATIONALLY MOBILE EPOXIDES

被引：30

作者：

CHEER, CJ

JOHNSON, CR

机构：

[1] Frank J. Seiler Research Laboratory, Office of Aerospace Research, U. S. Air Force Academy

[2] Department of Chemistry, Wayne State University, Detroit

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1968年 / 90卷 / 01期

关键词：

D O I：

10.1021/ja01003a031

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The syntheses and structural assignments of erythro- and threo-1-methyl-1-(hydroxyindanyl)oxirane are described. The course of the rearrangements of each of these isomers to 1- and 2-tetralone derivatives utilizing homogeneous (boron trifluoride) and heterogeneous (alumina) catalyses have been examined. The latter effects the arrangements in a stereoselective manner lending support to an earlier suggestion that such reactions proceed through conformationally immobile surface absorbed transition states. © 1968, American Chemical Society. All rights reserved.

引用

页码：178 / &

共 16 条

[1] NUCLEAR MAGNETIC RESONANCE STUDIES OF HYDROGEN BONDING IN ETHANOL
BECKER, ED
LIDDEL, U
SHOOLERY, JN
[J]. JOURNAL OF MOLECULAR SPECTROSCOPY, 1958, 2 (01) : 1 - 8
[2] A RING-EXPANSION REACTION . REARRANGEMENT OF 1-ISOPROPENYLCYCLOALKANOL EPOXIDES
CHEER, CJ
JOHNSON, CR
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (02) : 428 - &
[3] A RE-EXAMINATION OF THE PEROXYACID CLEAVAGE OF KETONES .1. RELATIVE MIGRATORY APTITUDES
HAWTHORNE, MF
EMMONS, WD
MCCALLUM, KS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (23) : 6393 - 6398
[4] *AUTOXYDATION VON KOHLENWASSERSTOFFEN .10. UBER PEROXYDE VON BENZOLDERIVATEN
HOCK, H
LANG, S
KNAUEL, G
[J]. CHEMISCHE BERICHTE-RECUEIL, 1950, 83 (03): : 227 - 237
[5] PROTON MAGNETIC RESONANCE STUDIES OF THE HYDROGEN BONDING OF PHENOL, SUBSTITUTED PHENOLS AND ACETIC ACID
HUGGINS, CM
PIMENTEL, GC
SHOOLERY, JN
[J]. JOURNAL OF PHYSICAL CHEMISTRY, 1956, 60 (8-9) : 1311 - 1314
[6] CALCULATION OF NUCLEAR MAGNETIC RESONANCE SPECTRA OF AROMATIC HYDROCARBONS
JOHNSON, CE
BOVEY, FA
[J]. JOURNAL OF CHEMICAL PHYSICS, 1958, 29 (05) : 1012 - 1014
[7] CHLORINATIVE RING EXPANSION . REACTION OF T-BUTYL HYPOCHLORITE + 1-VINYLCYCLOALKANOLS
JOHNSON, CR
GOLDSMITH, DJ
CHEER, CJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (11) : 3320 - &
[8] Polymethyl aromatic hydrocarbons. I. Synthesis of 1,2,4-trimethylnaphthalene and 1,2-, 1,3-and 1,4-dimethylnaphthalene
Kloetzel, MC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1940, 62 : 1708 - 1713
[9] THE HYDROGEN BOND .1. INTRAMOLECULAR AND INTERMOLECULAR HYDROGEN BONDS IN ALCOHOLS
KUHN, LP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (10) : 2492 - 2499
[10] MOUSSERONCANET M, 1965, CR HEBD ACAD SCI, V260, P4225

← 1 2 →