Thermal Interconversion of Phenylcarbene and Tropylidene. Preliminary communication | Zendy

Wentrup C. | Zendy; Wilczek K. | Zendy

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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 ).

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