A photochemical diels—alder reaction of N-methyltriazolinedione

Irradiation of N-methyltriazolinedione (MTAD) and naphthalene leads to a new [4 + 2] cycloadduct. Quantum yield data indicate that the reaction can occur via both singlet and triplet excited MTAD and also via charge transfer irradiation of a ground state complex. Naphthalene quenches the fluorescenc...

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Bibliographic Details
Published in:Journal of photochemistry 1985-01, Vol.28 (2), p.205-214
Main Authors: Kjell, D.P., Sheridan, R.S.
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
General and physical chemistry
Photochemistry
Physical chemistry of induced reactions (with radiations, particles and ultrasonics)
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Summary:Irradiation of N-methyltriazolinedione (MTAD) and naphthalene leads to a new [4 + 2] cycloadduct. Quantum yield data indicate that the reaction can occur via both singlet and triplet excited MTAD and also via charge transfer irradiation of a ground state complex. Naphthalene quenches the fluorescence of 1MTAD at diffusion-controlled rates. A contact radical–ion pair is suggested as a common intermediate in the singlet and charge transfer reactions. Triplet sensitization of the cycloadduct caused di-π-methane rearrangement.
ISSN:0047-2670
DOI:10.1016/0047-2670(85)87032-5