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Propellanes. Part LXXI. Confirmation of predicted regiospecificity in Diels‐Alder reactions of certain propellanes with 4‐phenyl‐1,2,4‐triazoline‐3,5‐dione
Author(s) -
Ashkenazi Pnina,
Kaftory Menachem,
Sayraç Tuǧmaç,
Maier Günther,
Ginsburg David
Publication year - 1983
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.19830660839
Subject(s) - chemistry , cyclobutane , propellane , ring (chemistry) , epoxide , ether , diels–alder reaction , stereochemistry , oxygen atom , bicyclic molecule , medicinal chemistry , organic chemistry , molecule , catalysis
Two isomeric propellane epoxides 1a and 1b containing a cyclohexadiene ring are attacked by the title dienophile as predicted, syn to the five‐membered ether ring whose α‐hydrogens exert less repulsion than the α‐epoxy hydrogens or the epoxide oxygen, respectively, of the cyclobutane ring.