Photolysis of the azo‐precursors of 2,3‐ and 1,8‐naphtoquinodimethane. Preliminary communication
- 1 January 1976
- journal article
- research article
- Published by Wiley in Helvetica Chimica Acta
- Vol. 59 (6) , 2273-2277
- https://doi.org/10.1002/hlca.19760590644
Abstract
A novel oxidation method for the synthesis of labile azo‐alkanes is reported. Matrix‐isolated 2,3‐naphthoquinodimethane is obtained by photolysis of 1,4‐dihydrobenzo[g]‐phthalazine in a rigid matrix (EPA glass) at 77 K and the electronic structure of its ground and lowest excited states is discussed. Nitrogen elimination from 1,4‐dihydronaphtho[1,8‐de][1,2]‐diazepine to yield acenaphthene occurs exclusively upon ππ* excitation while irradiation in the n‐π* absorption region induces cis/trans isomerization of the azo‐moiety. Neither ns flash nor low‐temperature photolysis provide evidence for the occurrence of 1,8‐naphthoquinodimethane as an intermediate in the formation of acenaphthene.Keywords
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