Cyclohexynes. Generation from iodonium salts and regioselective reaction with nucleophile

被引：21

作者：

Fujita, M ^{[1
]}

Sakanishi, Y ^{[1
]}

Kim, WH ^{[1
]}

Okuyama, T ^{[1
]}

机构：

[1] Himeji Inst Technol, Grad Sch Sci, Kamigori, Hyogo 6781297, Japan

来源：

CHEMISTRY LETTERS | 2002年 / 09期

关键词：

D O I：

10.1246/cl.2002.908

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Cyclohexynes are effectively generated by treatment of cyclohex-1-enyliodonium salts with a mild base such as acetate and fluoride ion in chloroform. Regioselectivity of the nucleophilic addition of acetate ion to cyclohexynes depends on the 4-substituent.

引用

页码：908 / 909

页数：2

共 35 条

[1] NUCLEOPHILIC-SUBSTITUTION OF AMINES ON 1-HALOCYCLOALKENES IN PRESENCE OF BASES IN TETRAHYDROFURAN [J].

BRUNET, JJ ;

FIXARI, B ;

CAUBERE, P .

TETRAHEDRON, 1974, 30 (16) :2931-2937

[2] NUCLEOPHILIC SUBSTITUTIONS ON 1-CHLOROCYCLOHEXENES IN PERSENCE OF BASES IN TETRAHYDROFURAN .2. STUDY ON SUBSTITUTED 1-CHLOROCYCLOHEXENES - SYNTHESIS OF CYCLOHEXYNE [J].

CAUBERE, P ;

BRUNET, JJ .

TETRAHEDRON, 1971, 27 (15) :3515-&

[3] UNIMETAL SUPER BASES [J].

CAUBERE, P .

CHEMICAL REVIEWS, 1993, 93 (06) :2317-2334

[4] ALKYLATION OF KETONE ENOLATES BY ALKYL CHLOROCYCLOHEXENES - INTERVENTION OF CYCLOHEXYNES AND-OR 1,2-CYCLOHEXADIENES [J].

FIXARI, B ;

BRUNET, JJ ;

CAUBERE, P .

TETRAHEDRON, 1976, 32 (08) :927-934

[5] Mechanism of racemization in the reaction of 4-methylcyclohexylidenemethyliodonium salt with sulfonate ions: Formation of intermediate cycloheptyne [J].

Fujita, M ;

Sakanishi, Y ;

Okuyama, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (37) :9190-9191

[6] CHEMISTRY OF BENT BONDS .45. NORBORNYNE [J].

GASSMAN, PG ;

VALCHO, JJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (16) :4768-4770

[7] SYMMETRY OF A REACTIVE INTERMEDIATE FROM RING EXPANSION OF CYCLOBUTYLIDENECARBENE - CYCLOPENTYNE [J].

GILBERT, JC ;

BAZE, ME .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (03) :664-665

[8] Pericyclic reactions of free and complexed cyclopentyne [J].

Gilbert, JC ;

Hou, DR ;

Grimme, JW .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (05) :1529-1534

[9] The nature of cyclopentyne from different precursors [J].

Gilbert, JC ;

McKinley, EG ;

Hou, DR .

TETRAHEDRON, 1997, 53 (29) :9891-9902

[10]

GILCHRIST TL, 1983, CHEM TRIPLE BONDED 1, P383

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