A novel photochemical vinylcyclopropane rearrangement yielding 6,7-dihydro-5H-benzocycloheptene derivatives

被引：18

作者：

Armesto, D ^{[1
]}

Ramos, A ^{[1
]}

Mayoral, EP ^{[1
]}

Ortiz, MJ ^{[1
]}

Agarrabeitia, AR ^{[1
]}

机构：

[1] Univ Complutense Madrid, Fac Ciencias Quim, Dept Quim Organ 1, E-28040 Madrid, Spain

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 02期

关键词：

D O I：

10.1021/ol991277a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1-Substituted 1-(2,2-diphenylvinyl)cyclopropanes with electron accepting groups at C1 undergo a novel rearrangement to benzocycloheptenes on triplet sensitized irradiation. In some instances competition between rearrangement to cyclopentenes and formation of cycloheptenes takes place. When electron acceptor groups are not present at C1, conventional ring opening to cyclopentenes occurs exclusively, A mechanism involving intramolecular SET from the diphenylvinyl unit to the electron-acceptor group is proposed for this novel photoreaction.

引用

页码：183 / 186

页数：4

共 18 条

[1]

[Anonymous], COMPREHENSIVE ORGANI

[2] A STUDY OF THE COMPETITION BETWEEN THE DI-PI-METHANE AND THE AZADI-PI-METHANE PROCESSES IN 2-VINYL-BETA,GAMMA-UNSATURATED OXIME DERIVATIVES - THE NOVEL AZADI-PI-METHANE REACTIVITY OF GAMMA-UNSATURATED OXIMES [J].

ARMESTO, D ;

ORTIZ, MJ ;

RAMOS, A ;

HORSPOOL, WM ;

MAYORAL, EP .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (26) :8115-8124

[3] Photochemical vinylcyclopropane rearrangements of 1-substituted-3-(2,2-diphenylvinyl)-2,2-dimethylcyclopropanes to cyclopentenes and different heterocycles [J].

Armesto, D ;

Ortiz, MJ ;

Agarrabeitia, AR .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (03) :1056-1060

[4] A novel photochemical synthesis of 5,6-dihydro-4H-1,2-oxazines by DCA-sensitized irradiation of gamma,delta-unsaturated oximes [J].

Armesto, D ;

Austin, MA ;

Griffiths, OJ ;

Horspool, WM ;

Carpintero, M .

CHEMICAL COMMUNICATIONS, 1996, (24) :2715-2716

[5]

Armesto D, 1995, RECL TRAV CHIM PAY B, V114, P514

[6]

ARMESTO D, 1995, CRC HDB ORGANIC PHOT, P915

[7] TETRAMETHYL 1,1,4,4-CYCLOHEXANETETRACARBOXYLATE - PREPARATION AND CONVERSION TO KEY PRECURSORS OF FLUORINATED, STEREOCHEMICALLY DEFINED CYCLOHEXANES [J].

DAVIS, CR ;

SWENSON, DC ;

BURTON, DJ .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (24) :6843-6850

[8] VINYLCYCLOPROPANE REARRANGEMENTS [J].

GOLDSCHMIDT, Z ;

CRAMMER, B .

CHEMICAL SOCIETY REVIEWS, 1988, 17 (03) :229-267

[9] STEREOCHEMISTRY OF PHOTOINDUCED AND MICHAEL ADDITION OF METHANOL TO 7-MEMBERED AND 8-MEMBERED 2-CYCLOALKENONES [J].

HART, H ;

DUNKELBLUM, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (16) :5141-5147

[10]

Hudlicky T., 1992, ORG REACT, V41, P1, DOI DOI 10.1002/0471264180.0R041.01

← 1 2 →