PHOSPHONIC SYSTEMS .9. SOLUTION AND SOLID-STATE STRUCTURE OF R,R (S,S) STEREOISOMERS OF THE ADDUCTS OF DIETHYL(1-CYCLOHEXENYL)METHYLPHOSPHONATE AND ALDEHYDES

被引：8

作者：

GERBER, KP ^{[1
]}

ROOS, HM ^{[1
]}

MODRO, TA ^{[1
]}

机构：

[1] UNIV PRETORIA,CTR HETEROATOM CHEM,DEPT CHEM,PRETORIA 0002,SOUTH AFRICA

来源：

JOURNAL OF MOLECULAR STRUCTURE | 1993年 / 296卷 / 1-2期

关键词：

D O I：

10.1016/0022-2860(93)80121-B

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The solution and solid state structures of single stereoisomers of alpha-adducts of diethyl(1-cyclohexenyl)methylphosphonate and three aldehydes were determined by NMR spectroscopy and by X-ray diffraction. In both phases, the molecules exist in virtually the same conformation, involving gauche orientation of the PO3Et2 and the 2-hydroxy groups, and trans orientation of the former group and the R group of the aldehyde molecule. In the crystal, this conformation is retained in spite of the fact that P=O ... H-O hydrogen bonding occurs inter- and not intramolecularly.

引用

页码：85 / 93

页数：9

共 14 条

[1]

ALCUDIA F, 1989, J MOL STRUC-THEOCHEM, V186, P211

[2] STEREOSPECIFICITY IN MIGRATION OF A CHIRAL PHOSPHINOYL GROUP TO A CHIRAL CARBON-ATOM - X-RAY CRYSTAL-STRUCTURE DETERMINATION OF REAGENT AND PRODUCT [J].

ALLEN, F ;

KENNARD, O ;

NASSIMBE.L ;

SHEPHERD, R ;

WARREN, S .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1974, (12) :1530-1536

[3] SOLVATION AND METAL-ION EFFECTS ON STRUCTURE AND REACTIVITY OF PHOSPHORYL COMPOUNDS .1. BETA-SUBSTITUTED ALKYLPHOSPHONIC ESTERS [J].

BELCIUG, MP ;

MODRO, AM ;

MODRO, TA ;

WESSELS, PL .

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 1992, 5 (12) :787-794

[4] STEREOCHEMISTRY OF ORGANIC SULFUR-COMPOUNDS .13. CONFIGURATIONAL ASSIGNMENT OF DIASTEREOISOMERS OF 2-METHYLSULPHINYL-1,2-DIPHENYLETHANOL AND OF THEIR ORTHO-METHYL AND ORTHO-ACETYL DERIVATIVES [J].

BRUNET, E ;

RUANO, JLG ;

MARTINEZ, MC ;

RODRIGUEZ, JH ;

ALCUDIA, F .

TETRAHEDRON, 1984, 40 (11) :2023-2034

[5]

CORBRIDGE DEC, 1974, STRUCTURAL CHEM PHOS, P251

[6]

GERBER JP, UNPUB

[7] THE RELATIONSHIP BETWEEN PROTON-PROTON NMR COUPLING-CONSTANTS AND SUBSTITUENT ELECTRONEGATIVITIES .1. AN EMPIRICAL GENERALIZATION OF THE KARPLUS EQUATION [J].

HAASNOOT, CAG ;

DELEEUW, FAAM ;

ALTONA, C .

TETRAHEDRON, 1980, 36 (19) :2783-2792

[8] REVISED METHOD FOR CALCULATION OF GROUP ELECTRONEGATIVITIES [J].

INAMOTO, N ;

MASUDA, S .

CHEMISTRY LETTERS, 1982, (07) :1003-1006

[9]

JOHNSON CK, 1965, ORNL3794 REP

[10] PHOSPHONIC SYSTEMS .8. SOLUTION AND SOLID-STATE CONFORMATION OF DIASTEREOMERIC ADDUCTS OF DIETHYL PROP-2-ENYLPHOSPHONATE TO P-NITROBENZALDEHYDE [J].

MULLER, EL ;

ROOS, HM ;

MODRO, TA .

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 1993, 6 (01) :64-70

← 1 2 →