PHOTOCHEMISTRY OF ISOTHIOCHROMAN-4-ONE

被引：45

作者：

LUMMA, WC

BERCHTOL.GA

机构：

[1] Department of Chemistry, Massachusetts Institute of Technology, Cambridge

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1969年 / 34卷 / 06期

关键词：

D O I：

10.1021/jo01258a007

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Irradiation of isothiochroman-4-one in cyclohexane (high pressure mercury lamp, Pyrex 7740 filter) produced thiochroman-3-one (21%). Under similar conditions 7-methoxy-, 8-methyl-, 3-methyl-, and 3,3-dimethyl-isothiochroman-4-one rearranged to 6-methoxy- (40%), 5-methy1- (30%), 2-methy1- (30%), and 2,2-dimethyl-thiochroman-3-one (37%), respectively. 1,2,3,4-Tetrahydro-1-keto-3-thiaphenanthrene failed to undergo the rearrangement reaction. Irradiation of 5-methyl-2,3-dihydro-2H,6H-thiopyran-3-one under similar conditions resulted in rearrangement to 2-(2-prop-1-enyl)-1-thietan-3-one (28-35%). The pathway for the photochemical conversion of isothiochroman-4-ones into thiochroman-3-ones is discussed. © 1969, American Chemical Society. All rights reserved.

引用

页码：1566 / &

共 24 条

[1] ULTRAVIOLET ABSORPTION SPECTRA OF SATURATED DISULPHIDES AND DISELENIDES [J].

BERGSON, G ;

SCHOTTE, L ;

CLAESON, G .

ACTA CHEMICA SCANDINAVICA, 1962, 16 (05) :1159-+

[2]

BERGSON G, 1961, ARKIV KEMI, V18, P489

[3]

BIRCH SF, 1954, I PETROL J, V40, P76

[4] SYNTHESIS AND FUNGISTATIC ACTIVITY OF SOME 5-(1-METHYL-2-THIOALKYLETHYLIDENE)-RHODANINES [J].

BRADSHER, CK ;

BROWN, FC ;

GRANTHAM, RJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (01) :114-115

[5]

CAGNIANT P, 1959, B SOC CHIM FR, P1998

[6]

CAGNIANT P, 1961, B SOC CHIM FR, P2225

[7] THE ULTRAVIOLET ABSORPTION SPECTRA OF ORGANIC SULFUR COMPOUNDS .1. COMPOUNDS CONTAINING THE SULFIDE FUNCTION [J].

FEHNEL, EA ;

CARMACK, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1949, 71 (01) :84-93

[8] THE ULTRAVIOLET ABSORPTION SPECTRA OF ORGANIC SULFUR COMPOUNDS .2. COMPOUNDS CONTAINING THE SULFONE FUNCTION [J].

FEHNEL, EA ;

CARMACK, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1949, 71 (01) :231-237

[9] SUBSTITUENT EFFECTS IN SOLVOLYSIS AND THIOSULFATE REACTIONS OF 3-,4- AND 3,5-SUBSTITUTED ALPHA-CHLOROTOLUENES [J].

FUCHS, R ;

CARLTON, DM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (01) :104-&

[10] MECHANISMS OF PHOTOREACTIONS IN SOLUTION .6. REDUCTION OF 1-NAPHTHALDEHYDE AND 2-ACETONAPHTHONE [J].

HAMMOND, GS ;

LEERMAKERS, PA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (02) :207-&

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