Premium
Thermal Interconversion of Phenylcarbene and Tropylidene. Preliminary communication
Author(s) -
Wentrup C.,
Wilczek K.
Publication year - 1970
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.19700530628
Subject(s) - chemistry , fluorene , contraction (grammar) , anthracene , ring (chemistry) , stereochemistry , photochemistry , organic chemistry , polymer , medicine
Phenylcarbene and tropylidene interconvert in the gas‐phase, as evidenced by the formation of stilbene and heptafulvalene ( 5 ) from both at 300°. Heptafulvalene itself rearranges to stilbene and anthracene above 500°. Phenylcarbene, but not tropylidene, undergoes ring contraction to fulvenallene ( 9 ) at 900°. Formation of fluorene from diphenylcarbene involves a complete ring expansion to 2‐phenyltropylidene ( 14 ), and subsequent ring contraction to 2‐biphenylylcarbene ( 15 ).