UNEXPECTED OPPOSITE STEREOCHEMISTRIES AND DIFFERENT MECHANISMS OF NUCLEOPHILIC-SUBSTITUTION REACTIONS OF HOMOCHIRAL TERT-BUTYLPHENYLTHIOPHOSPHINOYL CHLORIDE AND BROMIDE

被引：10

作者：

OMELANCZUK, J ^{[1
]}

MIKOLAJCZYK, M ^{[1
]}

机构：

[1] POLISH ACAD SCI,CTR MOLEC & MACROMOLEC STUDIES,PL-90363 LODZ,POLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1994年 / 19期

关键词：

D O I：

10.1039/c39940002223

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Reactions of ethylmercapto (ethylsulfanyl) anion with homochiral (+)-(S)-fert-butylphenylphosphinochloridothionate 2 and (-)-(S)-tert-butylphenylphosphinobromidothionate 3 proceed with inversion and retention at phosphorus, respectively, as a consequence of different reaction mechanisms; the stereoretentive reaction with bromide 3, in contrast to the direct nucleophilic substitution at phosphorus in chloride 2, is a two-step process involving in the first step nucleophilic attack of EtS(-) at the electropositive bromine atom.

引用

页码：2223 / 2224

页数：2

共 18 条

[1] ALKALINE HYDROLYSIS OF ALKOXY(METHYLTHIO)PHOSPHONIUM SALTS WITH RETENTION OF CONFIGURATION AT PHOSPHORUS [J].

DEATH, NJ ;

ELLIS, K ;

SMITH, DJH ;

TRIPPETT, S .

JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1971, (13) :714-&

[2] PROPERTIES AND MAPS OF STEREOCHEMICAL REACTION CYCLES THAT INVOLVE COMPOUNDS WITH 4 LIGANDS ATTACHED TO A TETRAHEDRAL CHIRAL CENTER [J].

GARWOOD, DC ;

CRAM, DJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (15) :4575-&

[3] PHOSPHORUS STEREOCHEMISTRY MECHANISTIC IMPLICATIONS OF THE OBSERVED STEREOCHEMISTRY OF BOND FORMING AND BREAKING PROCESSES AT PHOSPHORUS IN SOME 5-MEMBERED AND 6-MEMBERED CYCLIC PHOSPHORUS ESTERS [J].

HALL, CR ;

INCH, TD .

TETRAHEDRON, 1980, 36 (14) :2059-2095

[4] CHEMICAL-SHIFT NON-EQUIVALENCE OF ENANTIOMERS IN PROTON MAGNETIC-RESONANCE SPECTRA OF PARTLY RESOLVED PHOSPHINOTHIOIC ACIDS [J].

HARGER, MJP .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1978, (04) :326-331

[5] THE PROTON MAGNETIC-RESONANCE SPECTRA OF CHIRAL PHOSPHINATE ESTERS - CHEMICAL-SHIFT NON-EQUIVALENCE OF ENANTIOMERS INDUCED BY OPTICALLY-ACTIVE PHOSPHINOTHIOIC ACIDS [J].

HARGER, MJP .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1980, (10) :1505-1511

[6] SYNTHESIS OF OPTICALLY-ACTIVE PHOSPHORUS-COMPOUNDS VIA METAL PHOSPHINITES GENERATED BY REACTION OF OPTICALLY-ACTIVE SELENOPHOSPHINATES WITH PHENYLLITHIUM [J].

KAWASHIMA, T ;

IWANAGA, H ;

OKAZAKI, R .

CHEMISTRY LETTERS, 1993, (09) :1531-1532

[7] REACTION OF THIOLO AND SELENOLO ESTERS OF PHOSPHORUS-ACIDS WITH HALOGENS .2. INTERACTION OF S-METHYL TERT-BUTYL(PHENYL)PHOSPHINOTHIOLATES AND DI-TERT-BUTYL-PHOSPHINOTHIOLATES WITH ELEMENTAL BROMINE AND IODINE [J].

KRAWIECKA, B ;

WOJNATADEUSIAK, E .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1990, (02) :301-309

[8] OPTICALLY-ACTIVE PHOSPHINE SULFIDES FROM PHOSPHINE OXIDES AND BORON TRISULFIDE [J].

MARYANOF.BE ;

TANG, R ;

MISLOW, K .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1973, (08) :273-274

[9] STEREOSELECTIVE DESELENIZATION OF TERT-BUTYLPHENYLPHOSPHINOSELENOIC ACIDS - STEREOCHEMICAL RELATIONSHIP BETWEEN TERT-BUTYLPHENYLPHOSPHINOSELENOIC ACIDS AND THEIR SULFUR ANALOGUES [J].

MICHALSKI, J ;

SKRZYPZYNSKI, Z .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1975, 97 (02) :C31-C32

[10]

MICHALSKI J, 1966, ANGEW CHEM, V78, P716

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