Selectivity on the reaction of vinylic tellurides with butyllithium in the presence of carbonyl compounds.

被引：17

作者：

Dabdoub, MJ

Jacob, RG

Ferreira, JTB

Dabdoub, VB

Marques, FD

机构：

[1] Univ Sao Paulo, FFCLRP, Dept Quim, Lab Sintese Compostos Organocalcogenios, BR-14049 Ribeirao Preto, SP, Brazil

[2] Univ Fed Parana, Dept Quim, BR-80060000 Curitiba, Parana, Brazil

[3] Univ Fed Sao Carlos, Dept Quim, BR-13560 Sao Carlos, SP, Brazil

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 40期

关键词：

D O I：

10.1016/S0040-4039(99)01567-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The treatment of isomeric vinylic tellurides 5-7 with butyllithium in THF at -78 degrees C in the presence of a carbonyl compound such as benzaldehyde or cyclohexanone was studied. High selectivity of the attack at the tellurium atom was observed. In most cases, the corresponding allylic alcohol was obtained as the only (or major) product instead of the alcohols derived by the 1,2 addition of BuLi at the carbonyl compound. Similar results were obtained using the ketenetelluroacetal 14 instead of the vinylic monotellurides. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：7159 / 7162

页数：4

共 20 条

[1]

ARAUJO MA, 1995, SYNLETT, P1145

[2] HYDROTELLURATION OF ACETYLENES - SYNTHESIS OF VINYLIC TELLURIDES, DIVINYL TELLURIDES, AND 1-(ORGANYLTELLURO)-1,3-BUTADIENES [J].

BARROS, SM ;

DABDOUB, MJ ;

DABDOUB, VMB ;

COMASSETO, JV .

ORGANOMETALLICS, 1989, 8 (07) :1661-1665

[3] VINYLLITHIUMS FROM BUTYL-VINYL TELLURIDES AND BIS-VINYL TELLURIDES [J].

BARROS, SM ;

COMASSETO, JV ;

BERRIEL, J .

TETRAHEDRON LETTERS, 1989, 30 (52) :7353-7356

[4]

CHIEFFI A, 1994, TETRAHEDRON LETT, V35, P1993

[5] Vinylic selenides and tellurides - Preparation, reactivity and synthetic applications [J].

Comasseto, JV ;

Ling, LW ;

Petragnani, N ;

Stefani, HA .

SYNTHESIS-STUTTGART, 1997, (04) :373-&

[6] TRANSMETALATION BETWEEN VINYLIC TELLURIDES AND HIGHER-ORDER CYANOCUPRATES - INSITU FORMATION OF VINYL CUPRATES [J].

COMASSETO, JV ;

BERRIEL, JN .

SYNTHETIC COMMUNICATIONS, 1990, 20 (11) :1681-1685

[7] Hydrozirconation of acetylenic chalcogenides. Synthesis and reactions of zirconated vinyl chalcogenide intermediates [J].

Dabdoub, MJ ;

Begnini, ML ;

Guerrero, PG .

TETRAHEDRON, 1998, 54 (11) :2371-2400

[8] SYNTHESIS OF (E)-VINYLIC TELLURIDES AND THEIR TRANSFORMATION INTO ALPHA,BETA-UNSATURATED ESTERS AND CARBOXYLIC-ACIDS [J].

DABDOUB, MJ ;

BEGNINI, ML ;

CASSOL, TM ;

GUERRERO, PG ;

SILVEIRA, CC .

TETRAHEDRON LETTERS, 1995, 36 (42) :7623-7626

[9] Iodocyclization of (Z)-1-(butyltelluro)-1,4-diorganylbut-1-en-3-ynes. Synthesis and reactions of 3-iodotellurophenes [J].

Dabdoub, MJ ;

Dabdoub, VB ;

Pereira, MA ;

ZukermanSchpector, J .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) :9503-9511

[10] (1Z,3Z)-buta-1,3-dienyl-1-lithium species and substituted tellurophenes by Te/Li exchange on (1Z,3Z)-butyltelluro-1,3-butadienes and (1Z,3Z)-1,4-bis(butyltelluro)-1,3-butadienes. [J].

Dabdoub, MJ ;

Dabdoub, VB ;

Guerrero, PG ;

Silveira, CC .

TETRAHEDRON, 1997, 53 (12) :4199-4218

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