1H and 13C NMR spectral study of some 3-aryl-5r-aryl-6t-carbethoxycyclohex-2-enones - a study of four-bond 1H-1H couplings

被引：3

作者：

Yuvaraj, C. ^{[1
]}

Pandiarajan, K. ^{[1
]}

机构：

[1] Annamalai Univ, Dept Chem, Annamalainagar 608002, Tamil Nadu, India

来源：

MAGNETIC RESONANCE IN CHEMISTRY | 2011年 / 49卷 / 05期

关键词：

cyclohex-2-enones; H-1; NMR; C-13; four-bond H-1-H-1 coupling;

D O I：

10.1002/mrc.2724

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Nine 3-aryl-5r-aryl-6t-carbethoxycyclohex-2-enones 2a-2i have been synthesized. For all these compounds, H-1 and C-13 NMR spectra have been recorded. For two compounds, 2D spectra have been recorded. The spectral data suggest that these compounds adopt sofa conformation in solution with H-5, H-6 and H-4t occupying axial-like positions and H-4c occupying equatorial-like positions. In 3-phenyl-5r-(o-chlorophenyl)-6t-carbethoxycylohex-2-enone (2b), the o-chlorophenyl group is oriented such that the chlorine atom is in between H-4c and H-5. Allylic coupling of H-2 is observed only with H-4t. Evidence has been obtained for four-bond coupling between 1,3-diaxial and 1,3-axial-equatorial protons. Copyright (C) 2011 John Wiley & Sons, Ltd.

引用

页码：253 / 257

页数：5

共 16 条

[1] Ethyl 4-(4-bromophenyl)-6-r-phenyl-2-oxocyclohex-3-ene-1-t-carboxylate [J].

Anuradha, N. ;

Thiruvalluvar, A. ;

Yuvaraj, C. ;

Pandiarajan, K. ;

Butcher, R. J. .

ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 :O1896-U148

[2] Ethyl 6-r-(2-chlorophenyl)-2-oxo-4-phenylcyclohex-3-ene-1-t-carboxylate [J].

Anuradha, N. ;

Thiruvalluvar, A. ;

Pandiarajan, K. ;

Yuvaraj, C. .

ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2009, 65 :O191-U2948

[3] THE ANALYSIS OF NUCLEAR MAGNETIC RESONANCE SPECTRA .1. SYSTEMS OF 2 AND 3 NUCLEI [J].

BERNSTEIN, HJ ;

POPLE, JA ;

SCHNEIDER, WG .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1957, 35 (01) :65-81

[4] HYDROCYANATION OF SOME ALPHA,BETA-UNSATURATED KETONES, AND THE SYNTHESIS OF SOME UNUSUAL ISOXAZOLES [J].

COCKER, W ;

GRAYSON, DH ;

SHANNON, PVR .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (09) :1153-1162

[5] 1H and 13C NMR Spectral Study of Some 2r-Aryl-6c-phenylthian-4-ones, Their 1-Oxides and 1,1-Dioxides [J].

Devanathan, D. ;

Pandiarajan, K. .

SPECTROSCOPY LETTERS, 2009, 42 (03) :147-155

[6] Sulfogriseofulvin derivatives. Synthesis by [4+2]cycloaddition, structure, properties, crystal structure analysis, and antifungal activity of spiro[1,3-benzoxathiole-2,1'-cyclohex-2'-en]-4'-one 3,3-dioxides [J].

Friedrich, M ;

Meichle, W ;

Bernhard, H ;

Rihs, G ;

Otto, HH .

ARCHIV DER PHARMAZIE, 1996, 329 (07) :361-370

[7] SYNTHESES OF SUBSTITUTED SUCCINIMIDES BY RADICAL BETA-FRAGMENTATION OF BICYCLIC CARBINOL AMIDES - A NEW EXPEDITIOUS SYNTHESIS OF 2-[2-(METHOXYCARBONYL)ETHYL]-3-[(METHOXYCARBONYL)METHYL]3-METHYLSUCCINIMIDE, THE RING-B IMIDE OF VITAMIN-B-12 [J].

HERNANDEZ, R ;

SUAREZ, E ;

MELIAN, D .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (10) :2766-2772

[8]

Kamatchi S, 2009, INDIAN J CHEM B, V48, P553

[9] Substitution at the α-carbons of α,β-unsaturated carbonyl compounds:: anti-Michael addition [J].

Lewandowska, Elzbieta .

TETRAHEDRON, 2007, 63 (10) :2107-2122

[10]

Pandey SC, 2004, INDIAN J CHEM B, V43, P2705

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