Reaction of benzyne with styrene oxide:: Insertion of arynes into a C-O bond of epoxides

被引：35

作者：

Beltran-Rodil, Sandra ^{[1
]}

Pena, Diego ^{[1
]}

Guitian, Enrique ^{[1
]}

机构：

[1] Univ Santiago de Compostela, Fac Quim, Dept Quim Organ, Santiago De Compostela 15782, Spain

来源：

SYNLETT | 2007年 / 08期

关键词：

arynes; epoxides; furans; insertions; ring expansion;

D O I：

10.1055/s-2007-977460

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Benzyne inserts into one of the C-O bonds of styrene oxide to form a dihydrobenzofuran as the major product together with five other reaction products. A detailed study of the reaction mixture clarified an intriguing forty-year-old personal communication from Stiles and Haag.

引用

页码：1308 / 1310

页数：3

共 13 条

[1] RADICAL IONS IN PHOTOCHEMISTRY .19. 1,N-RADICAL IONS - THE PHOTOSENSITIZED (ELECTRON-TRANSFER) FORMATION OF 1,5-RADICAL CATIONS [J].

ARNOLD, DR ;

FAHIE, BJ ;

LAMONT, LJ ;

WIERZCHOWSKI, J ;

YOUNG, KM .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1987, 65 (12) :2734-2743

[2] FLUORIDE-INDUCED 1,2-ELIMINATION OF ORTHO-TRIMETHYLSILYLPHENYL TRIFLATE TO BENZYNE UNDER MILD CONDITIONS [J].

HIMESHIMA, Y ;

SONODA, T ;

KOBAYASHI, H .

CHEMISTRY LETTERS, 1983, (08) :1211-1214

[3]

Hoffmann R.W., 1967, DEHYDROBENZENE CYCLO

[4] Preparation of functionalized aryl magnesium reagents by the addition of magnesium aryl thiolates and amides to arynes [J].

Lin, WW ;

Sapountzis, I ;

Knochel, P .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (27) :4258-4261

[5] Intermolecular C-N addition of amides and S-N addition of sulfinamides to arynes [J].

Liu, ZJ ;

Larock, RC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (38) :13112-13113

[6]

Peña D, 2002, SYNTHESIS-STUTTGART, P1454

[7] Insertion of arynes into σ bonds [J].

Pena, Diego ;

Perez, Dolores ;

Guitian, Enrique .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (22) :3579-3581

[8]

STILES M, 1962, J ORG CHEM, V27, P4715

[9]

Stiles M., COMMUNICATION, P178

[10] The direct acyl-alkylation of arynes [J].

Tambar, UK ;

Stoltz, BM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (15) :5340-5341

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