ISSN:
0018-019X
Schlagwort(e):
Chemistry
;
Organic Chemistry
Quelle:
Wiley InterScience Backfile Collection 1832-2000
Thema:
Chemie und Pharmazie
Notizen:
Irradiation of 1-alkyl-substituted 1,2-dihydronaphthalenes (10, 11, 12) with a lowpressure mercury lamp yields by ring opening ω-vinyl-o-quinodimethanes, which undergo [1, 7] H-shifts to give 1,2-divinyl-benzenes (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 ω-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 and 7). 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 lowpressure 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 photreaction of the primarily formed ω-vinyl-o-quinodimethanes a.
Zusätzliches Material:
18 Tab.
Materialart:
Digitale Medien
URL:
http://dx.doi.org/10.1002/hlca.19710540771
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