Synthesis of Benzo[ g ]isochromenes through Photo‐Dehydro‐ Diels–Alder  Reaction | Zendy

Wessig Pablo | Zendy; Müller Gunnar | Zendy; Herre Robert | Zendy; Kühn Andreas | Zendy

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Synthesis of Benzo[ g ]isochromenes through Photo‐Dehydro‐ Diels–Alder Reaction

Author(s) -

Wessig Pablo,

Müller Gunnar,

Herre Robert,

Kühn Andreas

Publication year - 2006

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.200690241

Subject(s) - chemistry , regioselectivity , diels–alder reaction , reaction mechanism , computational chemistry , stereochemistry , organic chemistry , catalysis

The Photo‐Dehydro‐ Diels–Alder (PDDA) reaction is shown to be a versatile method for the preparation of highly functionalized naphthalenes. Thus, ketones 1 could be cyclized to the 1 H ‐benzo[ g ]isochromen‐4‐(3 H )‐ones 11 and 12 , mostly in good yields. The influence of various substituents on the regioselectivity of the reaction was investigated, and the mechanism is discussed based on theoretical calculations.

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