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A Novel Hydrocarbon, 8,10‐Dimethylidenetricyclo[7.1.1.0 2,7 ]undeca‐2,4,6‐triene: Synthesis of benzopinane skeleton via di‐π‐methane rearrangement of benzonorbornadiene system
Author(s) -
Altundaş Aliye,
Akbulut Nihat,
Balci Metin
Publication year - 1998
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.19980810504
Subject(s) - chemistry , hydrocarbon , methane , hydrolysis , medicinal chemistry , base (topology) , stereochemistry , organic chemistry , mathematical analysis , mathematics
The [4 + 2] cycloadduct 17 of 2,3‐dimethylidene‐1,2,3,4‐tetrahydro‐1,4‐methanonaphthalene and 4‐phenyl‐4 H ‐1,2,4‐triazole‐3,5‐dione (PTAD) was subjected to a triplet‐sensitized di‐π‐methane rearrangement. Hydrolysis of the resulting urazol 18 gave the hydrocarbon 7 . Hydrolysis of 18 at lower base concentrations led to isomeric stable semicarbazides 24 and 25 , which were submitted NiO 2 or MnO 2 oxidation, to give the target compound 7 , and oxidation products 26 and 27 .