Site and stereoselectivity of the cyclopropanation of unsymmetrically substituted 1,3-dienes by the Simmons-Smith reaction.

被引：4

作者：

Guerreiro, MC

Schuchardt, U

机构：

[1] Instituto de Química, Universidade Estadual de Campinas, 13083-970 - Campinas, SP

来源：

SYNTHETIC COMMUNICATIONS | 1996年 / 26卷 / 09期

关键词：

D O I：

10.1080/00397919608002620

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In the Simmons-Smith reaction, 1,3-dienes are preferentially cyclopropanated at the more electron-rich double bond to afford the trans-vinylcyclopropane; an allylic hydroxyl group increases the reactivity and directs the cyclopropanation to the adjacent double bond.

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页码：1793 / 1800

页数：8

相关论文

共 13 条

[1]

BERTRAND M, 1967, B SOC CHIM FR, P3549

[2]

BUCHEL KH, 1962, Z NATURFORSCH PT B, VB 17, P349

[3] NEW STEREOSPECIFIC SYNTHETIC ROUTES TO TRISUBSTITUTED OLEFINS [J].

COREY, EJ ;

YAMAMOTO, H ;

HERRON, DK ;

ACHIWA, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (22) :6635-&

[4]

Doyle M.P., 1986, CATALYSIS ORGANIC RE, P47

[5] REACTION OF METHYLENE WITH BUTA-1,3-DIENE [J].

GRZYBOWSKA, B ;

TROTMANDICKENSO.AF ;

KNOX, JH .

JOURNAL OF THE CHEMICAL SOCIETY, 1961, (OCT) :4402-+

[6]

GUERREIRO MC, 1993, THESIS U ESTADUAL CA

[7] REPLACEMENT OF CARBONYL OXYGEN OF HYDROXY KETONES BY METHYLENE AND 1,1-ETHANO GROUPS BY REACTION WITH SIMMONS-SMITH REAGENT [J].

HARRISON, IT ;

RAWSON, RJ ;

TURNBULL, P ;

FRIED, JH .

JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (23) :3515-&

[8] CYCLOPROPYL CONJUGATION IN OLEFINIC ESTERS . CONFORMATIONAL EFFECTS ON ULTRAVIOLET ABSORPTION [J].

JORGENSON, MJ ;

LEUNG, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (14) :3769-+

[9] UBER PROTONENKATALYSIERTE REAKTIONEN AN STEROID-CYCLOPROPYLALKOHOLEN [J].

LAURENT, H ;

MULLER, H ;

WIECHERT, R .

CHEMISCHE BERICHTE-RECUEIL, 1966, 99 (12) :3836-&

[10] MONOMERS AND POLYMERS, A SYNTHESIS OF VINYL CYCLOPROPANE AND DICYCLOPROPYL [J].

OVERBERGER, CG ;

HALEK, GW .

JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (03) :867-&