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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.