Poly[styrene(iodosodiacetate)]-promoted ring expansion reaction of 1-alky-nylcycloalkanols:: A novel synthesis of (Z)-2-(1-iodo-1-organyl)methylene-cycloalkanones

被引：27

作者：

Chen, JM

Huang, X

机构：

[1] Zhejiang Univ, Dept Chem, Hangzhou 310028, Peoples R China

[2] Gannan Teacher Coll, Dept Chem, Ganzhou 341000, Peoples R China

来源：

SYNTHESIS-STUTTGART | 2004年 / 15期

关键词：

poly[styrene(iodosodiacetate); ring expansion; 1-alkynyl substituted tertiary alcohols; 2-(1-iodo-1-organyl)methylenecycloalkanones;

D O I：

10.1055/s-2004-831214

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The ring expansion reaction of 1-alkynylcycloalkanols with poly [styrene(iodosodiacetate)] and iodine affords (Z)-2-(1-iodo-1-organyl)methylenecycloalkanones in moderate to good yields.

引用

页码：2459 / 2462

页数：4

共 11 条

[1] FORMATION OF A DIHALOENONE OF HOMOADAMANTANONE [J].

BOVONSOMBAT, P ;

MCNELIS, E .

SYNTHETIC COMMUNICATIONS, 1995, 25 (08) :1223-1229

[2] RING EXPANSION OF AN ALPHA-BROMOALKYNOL CAMPHOR BY MEANS OF IODINE AND KOSER REAGENT [J].

BOVONSOMBAT, P ;

MCNELIS, E .

TETRAHEDRON LETTERS, 1993, 34 (27) :4277-4280

[3] RING EXPANSIONS OF 2-HALOETHYNYL-2-NORBORNANOLS [J].

DJUARDI, E ;

BOVONSOMBAT, P ;

MCNELIS, E .

TETRAHEDRON, 1994, 50 (41) :11793-11802

[4] PHENYL SHIFTS TO VINYL CATIONS FORMED BY IODINATION OF ALKYNES [J].

JANAS, JJ ;

ASIRVATHAM, ET ;

MCNELIS, E .

TETRAHEDRON LETTERS, 1985, 26 (16) :1967-1968

[5]

MARQUAIS S, 1998, ORG SYNTH COLL, V9, P328

[6] A novel and general route to diverse A-ring aromatic trichothecanes via cyclobutanes [J].

Nemoto, H ;

Miyata, J ;

Fukumoto, K .

TETRAHEDRON, 1996, 52 (31) :10363-10374

[7] A novel palladium-mediated cascade reaction triggered by strain release of the cyclobutane system. A new general route to benzo- and naphthohydrindans [J].

Nemoto, H ;

Miyata, J ;

Yoshida, M ;

Raku, N ;

Fukumoto, K .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (22) :7850-7857

[8]

ORT O, 1993, ORG SYNTH, V8, P522

[9] Polymer-supported hypervalent iodine reagents [J].

Togo, H ;

Sakuratani, K .

SYNLETT, 2002, (12) :1966-1975

[10] Hypervalent iodine in synthesis XXVIII: The preparation and utility of polymer-supported phenyliodine(III) diacetate [J].

Wang, GP ;

Chen, ZC .

SYNTHETIC COMMUNICATIONS, 1999, 29 (16) :2859-2866

← 1 2 →