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[ 4 + 2] Cycloadditions of Substituted Homobenzoquinones with Cyclopentadiene
Author(s) -
Adam Waldemar,
Kliem Ulrike,
Lucchini Vittorio,
Peters EvaMaria,
Peters Karl,
Von Schnering Hans Georg
Publication year - 1988
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19881210608
Subject(s) - chemistry , cyclopentadiene , cyclopropane , stereoselectivity , steric effects , reactivity (psychology) , stereochemistry , nuclear overhauser effect , cycloaddition , benzoquinone , medicinal chemistry , nuclear magnetic resonance spectroscopy , organic chemistry , ring (chemistry) , catalysis , medicine , alternative medicine , pathology
The Diels‐Alder reaction of homobenzoquinones with cyano‐substituted cyclopropane rings and cyclopentadiene affords the endo/anti and the exo/syn cycloadducts, the former preferred by fourto fivefold. X‐ray structure analyses and nuclear Overhauser enhancements (NOE) were necessary to define the stereochemistry of these products. The lower reactivity and stereoselectivity compared to p ‐benzoquinone is attributed to unfavorable steric effects.