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Photolysis and Pyrolysis of N ‐Methyl Isoindole
Author(s) -
Rettig Wolfgang,
Wirz Jakob
Publication year - 1978
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19780610139
Subject(s) - chemistry , isoindole , photodissociation , dimer , pyrolysis , photochemistry , irradiation , isoquinoline , medicinal chemistry , organic chemistry , physics , nuclear physics
Near UV. irradiation of N ‐methyl isoindole ( 1 ) in deaerated solution has yielded two constitutionally isomeric [ π 4 s + π 4 s ] dimers 3 and 4 ( Scheme 2). No transient or stable photoisomers of 1 were detected. The photodimers were reconverted to 1 both by pyrolysis and photolysis. The photocleavage of dimer 3 proceeds (predominantly) by anonadiabatic pathway yielding 1 in its electronic ground state. Prolonged pyrolysis of 1 afforded 11 H ‐indeno [1,2‐ c ]‐isoquinoline ( 5 ) as a major product.