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Synthese und seitenselektive Diels‐Alder‐Reaktion von Homodehydroisodicyclopentadien
Author(s) -
Ipaktschi Junes,
Herber Jürgen,
Kalinowski HansOtto,
Boese Roland
Publication year - 1990
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.19901230215
Subject(s) - chemistry , cyclopentadiene , enone , ketone , diels–alder reaction , steric effects , adduct , yield (engineering) , mesylate , bicyclic molecule , medicinal chemistry , organic chemistry , catalysis , materials science , metallurgy
Synthesis and Face‐Selective Diels‐Alder Reaction of Homodehydroisodicyclopentadiene Under alkaline conditions the mesylate 6c , obtained from the tetracyclic ketone 6b fragments into the enone 8a . The latter is transformed via alcohol 9 into the homodehydroisodicyclopentadiene 3 and via tosylhydrazone 8b into the triene 4 . Cyclopentadiene 3 reacts with a series of non‐acetylenic dienophiles from the sterically less hindered side to give the products 14 ‐ 17 . Acetylenic dienophiles yield the adducts 19 – 22 in a 1:1 ratio. The UV and PE spectra of triene 4 are discussed.