CONFORMATIONAL PREFERENCES OF C1-OXYGENATED ACYCLIC CHIRAL ALKENES - THE EFFECT OF VINYL AND ALLYL SUBSTITUENTS

被引：19

作者：

GUNG, BW

WOLF, MA

OHM, K

PEAT, AJ

机构：

[1] Department of Chemistry, Miami University Oxford

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 09期

关键词：

D O I：

10.1016/S0040-4039(00)60307-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The conformational preferences of several chiral alkenes have been studied by the variable temperature NMR technique. Electron-withdrawing groups (EWG) enhance the C-O eclipsed form, and electron-releasing groups (ERG) favor the C-H eclipsed form in these C1-oxygenated chiral alkenes.

引用

页码：1417 / 1420

页数：4

共 12 条

[1] PROTON MAGNETIC RESONANCE SPECTRA OF OLEFINS .V. 3-CHLORO- AND 3-METHOXYPROPENES
BOTHNERBY, AA
CASTELLA.S
EBERSOLE, SJ
GUNTHER, H
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (11) : 2466 - +
[2] THE CONFORMATIONAL EQUILIBRIUM OF CHORISMATE IN SOLUTION - IMPLICATIONS FOR THE MECHANISM OF THE NONENZYMATIC AND THE ENZYME-CATALYZED REARRANGEMENT OF CHORISMATE TO PREPHENATE
COPLEY, SD
KNOWLES, JR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (16) : 5008 - 5013
[3] CONFORMATIONS .6. VINYL-ALLYLIC PROTON SPIN COUPLINGS
GARBISCH, EW
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (24) : 5561 - +
[4] GENERAL-METHOD FOR DETERMINING ABSOLUTE-CONFIGURATIONS OF ACYCLIC ALLYLIC ALCOHOLS
GONNELLA, NC
NAKANISHI, K
MARTIN, VS
SHARPLESS, KB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (13) : 3775 - 3776
[5] THE RELATIONSHIP BETWEEN PROTON-PROTON NMR COUPLING-CONSTANTS AND SUBSTITUENT ELECTRONEGATIVITIES .1. AN EMPIRICAL GENERALIZATION OF THE KARPLUS EQUATION
HAASNOOT, CAG
DELEEUW, FAAM
ALTONA, C
[J]. TETRAHEDRON, 1980, 36 (19) : 2783 - 2792
[6] VICINAL PROTON COUPLING IN NUCLEAR MAGNETIC RESONANCE
KARPLUS, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (18) : 2870 - 2871
[7] KHAN SD, 1987, J AM CHEM SOC, V109, P650
[8] CONFORMATIONAL-ANALYSIS OF 7-SUBSTITUTED 2-METHOXY-METHYLENECYCLOHEXANES - EVIDENCE AGAINST NO-]PI-STAR ORBITAL STABILIZATION OF THE AXIAL CONFORMER
LESSARD, J
SAUNDERS, JK
VIET, MTP
[J]. TETRAHEDRON LETTERS, 1982, 23 (20) : 2059 - 2062
[9] NUDELMAN A, 1982, SYNTHESIS-STUTTGART, P687
[10] CONFORMATIONS, POSSIBLE H-BONDING, AND MICROWAVE-SPECTRUM OF 3-BUTEN-2-OL
SMITH, Z
CARBALLO, N
WILSON, EB
MARSTOKK, KM
MOLLENDAL, H
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (07) : 1951 - 1957

← 1 2 →