Phototransformations of some 3-alkoxy-2-styrylchromones: type II cyclisations of 1,4-and 1,6-biradicals

被引：21

作者：

Gupta, SC ^{[1
]}

Yusuf, M ^{[1
]}

Sharma, S ^{[1
]}

Saini, A ^{[1
]}

Arora, S ^{[1
]}

Kamboj, RC ^{[1
]}

机构：

[1] Kurukshetra Univ, Dept Chem, Kurukshetra 136119, Haryana, India

来源：

TETRAHEDRON | 2004年 / 60卷 / 38期

关键词：

3-alkoxy-2-styrylchromones; type II cyclisations; 1,4-and 1,6-biradicals;

D O I：

10.1016/j.tet.2004.07.003

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

3-Alkoxy-2-styrylchromones on photo-irradiation with UV-light transform into oxetanopyrananones, pyranopyrones, pyranopyrananones and pyranoalcohols. The products formed have been found to depend upon the structure of alkoxy group (methyl, benzyl and allyls). Alkoxychromones containing a heterocyclic ring (thiophene, furan) in place of phenyl in the styryl group produced only pyranoalcohols as the photoproducts. The photo-conversions have been rationalized through an initial H-abstraction by the C=O group producing a 1,4-biradical. In allyloxy derivatives, cyclisations involve both 1,4- and 1,6-biradicals. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：8445 / 8454

页数：10

共 35 条

[1]

Algar J., 1934, Proc. R. Ir. Acad, V42B, P1

[2] PHOTOLYSIS OF LINEAR HETEROSUBSTITUTED CONJUGATED KETONES [J].

ARNOULD, JC ;

ENGER, A ;

FEIGENBAUM, A ;

PETE, JP .

TETRAHEDRON, 1979, 35 (21) :2501-2512

[3] INTRAMOLECULAR HYDROGEN ABSTRACTION IN KETONE PHOTOCHEMISTRY - THE 1ST EXAMPLES OF ZETA-HYDROGEN ABSTRACTION [J].

CARLESS, HAJ ;

MWESIGYEKIBENDE, S .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (21) :1673-1674

[4] PHOTOCHEMICAL REMOVAL OF METHOXY-GROUPS IN PYRANOSIDULOSES [J].

COLLINS, PM ;

GUPTA, P .

JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1969, (03) :90-&

[5] PHOTOCHEMISTRY OF ALPHA-METHYLENE KETONES - COMPETITIVE BETA-HYDROGEN AND GAMMA-HYDROGEN ABSTRACTION [J].

CORMIER, RA ;

AGOSTA, WC ;

SCHREIBE.WL .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1972, (12) :729-&

[6] SINGLET BIRADICAL INTERMEDIATES IN PHOTOCHEMISTRY OF ALPHA-METHYLENE KETONES [J].

CORMIER, RA ;

AGOSTA, WC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (02) :618-620

[7] PHOTOCHEMICAL REARRANGEMENTS OF ALPHA-METHYLENE KETONES [J].

CORMIER, RA ;

SCHREIBE.WL ;

AGOSTA, WC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (15) :4873-4884

[8]

COYLE JD, 1986, CHEM ROYAL SOC SPECI, V57

[9]

DEAN I, 1965, J CHEM SOC, P3978

[10] PHOTOLYSIS OF 2-ALKOXY-1,4-NAPHTHOQUINONES [J].

ELLIS, JV ;

JONES, JE .

JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (04) :485-488

← 1 2 3 4 →