Premium
Propellanes VIII. Electrocyclic Reactions of Tetraenic Propellanes
Author(s) -
Altman Janina,
Babad Esther,
Ginsburg D.,
Rubin M. B.
Publication year - 1969
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.196900056
Subject(s) - chemistry , ether , sequence (biology) , electrocyclic reaction , stereochemistry , irradiation , medicinal chemistry , polymer chemistry , bicyclic molecule , organic chemistry , biochemistry , physics , nuclear physics
The electrocyclic reaction sequence of tetraenic propellanes is analogous to that of their parent, cis‐9,10‐dihydronaphthalene as a member of the (CH) 10 family. Irradiation of Ia‐e afforded IIa‐e of which IIb and IIc have been isolated. These are the first stable derivatives of tetracyclo [4.4.0.0 2,10 .0 5,7 ]deca‐3,8‐diene. Thermal bond‐realignment of IIa‐e led, due to fluxional isomerism in prebullvalene and its derivatives, to prebullvalenes of the III series. Only in the case of the prebullvalene lactone was it possible to observe IVd alongside of IIId in its room terperature NMR spectrum. Irradiation of the prebullvalene ether IIIe afforded a bullvalene ether which at low temperature shows the presence of XIII (R=R=−CH 2 ‐O‐CH 2 ‐) and XV.