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Photochemisches Verhalten von 1- und 2-alkylierten 1,2-Dihydronaphtalinen


Heimgartner, Heinz; Ulrich, Linus; Hansen, Hans-Jürgen; Schmid, Hans (1971). Photochemisches Verhalten von 1- und 2-alkylierten 1,2-Dihydronaphtalinen. Helvetica Chimica Acta, 54(7):2313-2354.

Abstract

Irradiation of 1-alkyl-substituted 1,2-dihydronaphthalenes (10, 11, 12) with a low-pressure mercury lamp yields by ring opening omega-vinyl-o-quinodimethanes, which undergo [1,7]H-shifts to give 1,2-divinylbenzenes (8, 18, 23; cf. schemes 2, 3 and 4). In a further photoreaction of the divinylbenzenes, benzobicyclo[3.1.0]hex-2-enes (17, 19, 22) are formed. 2-Alkyl-substituted 1,2-dihydronaphthalenes (13, 14, 15, 16) are transformed by irradiation into o-vinyl-o-quinodimethanes, which show [1,7] H-shifts to yield in this case 2-(buta-1',3’-dienyl)toluenes (9, 25, 26, 27; cf. schemes 6 and7). The irradiation of 1-methyl-(10) and 1-ethyl-1,2-dihydronaphthalene (11) with a high-pressure mercury lamp produces, besides the products of irradiation using the low-pressure lamp, 2-ethyl-allenylbenzene (24), and (from 11) 4-exo-ethyl-benzobicyclo[3.1.0]hex-2- ene (exo-20) and 2-propyl-allenylbenzene (21), respectively (cf. scheme 5). Obviously, these products arise from a photoreaction of the primarily formed omega-vinyl-o-quinodimethanes a.

Abstract

Irradiation of 1-alkyl-substituted 1,2-dihydronaphthalenes (10, 11, 12) with a low-pressure mercury lamp yields by ring opening omega-vinyl-o-quinodimethanes, which undergo [1,7]H-shifts to give 1,2-divinylbenzenes (8, 18, 23; cf. schemes 2, 3 and 4). In a further photoreaction of the divinylbenzenes, benzobicyclo[3.1.0]hex-2-enes (17, 19, 22) are formed. 2-Alkyl-substituted 1,2-dihydronaphthalenes (13, 14, 15, 16) are transformed by irradiation into o-vinyl-o-quinodimethanes, which show [1,7] H-shifts to yield in this case 2-(buta-1',3’-dienyl)toluenes (9, 25, 26, 27; cf. schemes 6 and7). The irradiation of 1-methyl-(10) and 1-ethyl-1,2-dihydronaphthalene (11) with a high-pressure mercury lamp produces, besides the products of irradiation using the low-pressure lamp, 2-ethyl-allenylbenzene (24), and (from 11) 4-exo-ethyl-benzobicyclo[3.1.0]hex-2- ene (exo-20) and 2-propyl-allenylbenzene (21), respectively (cf. scheme 5). Obviously, these products arise from a photoreaction of the primarily formed omega-vinyl-o-quinodimethanes a.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:German
Date:1971
Deposited On:29 Dec 2014 15:07
Last Modified:08 Dec 2017 09:12
Publisher:Wiley-Blackwell Publishing, Inc.
ISSN:0018-019X
Funders:Schweizerischer Nationalfonds
Publisher DOI:https://doi.org/10.1002/hlca.19710540771

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