DIFFERENTIATION OF THE REACTIVITIES OF CARBON-CARBON MULTIPLE BONDS IN ONE MOLECULE - HIGHLY CHEMO-SELECTIVE AND STEREOSELECTIVE HYDROHALOGENATION OF ALLYL OR PROPARGYL PROPIOLATES

被引：30

作者：

MA, SM ^{[1
]}

LU, XY ^{[1
]}

机构：

[1] ACAD SINICA,SHANGHAI INST ORGAN CHEM,345 LINGLING LU,SHANGHAI 200032,PEOPLES R CHINA

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 52期

关键词：

D O I：

10.1016/S0040-4039(00)97323-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of allyl or propargyl propiolates with lithium halides in acetic acid afforded allyl or propargyl (Z)-3-halopropenoates highly chemo- and stereo-selectively by differentiation of reactivities of carbon-carbon multiple bonds in the same molecule.

引用

页码：7653 / 7656

页数：4

共 21 条

[1]

BIOUGNE J, 1971, CR ACAD SCI C CHIM, V272, P858

[2] TRANSMISSION OF POLAR EFFECTS .3. KINETICS OF ACID-CATALYZED ESTERIFICATION OF 3-SUBSTITUTED ACRYLIC ACIDS AND ALKALINE HYDROLYSIS OF METHYL ESTERS [J].

BOWDEN, K .

CANADIAN JOURNAL OF CHEMISTRY, 1966, 44 (06) :661-&

[3]

CHALCHAT JC, 1983, CR ACAD SCI II, V296, P253

[4] POLAR ADDITION OF HYDROGEN BROMIDE TO CYCLOHEXENE [J].

FAHEY, RC ;

SMITH, RA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (22) :5035-&

[5] HYDROCHLORINATION OF CYCLOHEXENE IN ACETIC ACID . KINETIC AND PRODUCT STUDIES [J].

FAHEY, RC ;

MONAHAN, MW ;

MCPHERSO.CA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (09) :2810-&

[6] REACTION OF ACETYLENES WITH HYDROGEN-CHLORIDE IN ACETIC-ACID - EFFECT OF STRUCTURE UPON ADE2 AND AD3 REACTION-RATES [J].

FAHEY, RC ;

PAYNE, MT ;

LEE, DJ .

JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (08) :1124-1130

[7] POLAR ADDITIONS TO OLEFINS AND ACTYLENES .3. KINETICS AND STEREOCHEMISTRY OF ADDITION IN SYSTEM 1-PHENYLPROPYNE-HYDROGEN CHLORIDE-ACETIC ACID [J].

FAHEY, RC ;

LEE, DJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (23) :5555-&

[8] MECHANISM OF HYDROCHLORINATION OF T-BUTYLETHYLENE AND STYRENE IN ACETIC ACID [J].

FAHEY, RC ;

MCPHERSO.CA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (14) :3865-&

[9]

KUITZ AN, 1965, J ORG CHEM, V30, P3141

[10]

MA S, IN PRESS J CHEM SOC

← 1 2 3 →