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Photosensitized cyclodimerizations of 4‐vinylpyridine, 2‐vinylpyridine, and 2‐vinylquinoline
Author(s) -
Nakano Tatsuhiko,
Martín A.,
Rivas C.,
Pérez C.
Publication year - 1977
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570140539
Subject(s) - benzophenone , chemistry , dimer , benzene , solvent , methanol , alcohol , photochemistry , irradiation , proton nmr , medicinal chemistry , polymer chemistry , organic chemistry , physics , nuclear physics
Irradiations of 4‐vinylpyridine and of 2‐vinylpyridine in either f‐butyl alcohol or benzene, with benzophenone, yielded a single photodimer, which, on the basis of the nmr and mass spectral data, was assigned the trans ‐head‐to‐head structure (I). Upon irradiation in either t ‐butyl alcohol or benzene, in the presence of benzophenone, 2‐vinylquinoline gave a single photodimer whose structure and stereochemistry were also determined from the nmr and mass spectral evidence as (V). Irradiation of 2‐vinylquinoline in benzene, in the absence of benzophenone, also gave rise to the same photodimer, but, when t‐butyl alcohol or methanol was used as a solvent, no dimer formation was observed.