Reaction of 4‐phenyl‐1,2,4‐triazoline‐3,5‐dione (PTAD) with bicyclic monoterpenes | Zendy

Adam Waldemar | Zendy; De Lucchi Ottorino | Zendy; Hill Karlheinz | Zendy

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Reaction of 4‐phenyl‐1,2,4‐triazoline‐3,5‐dione (PTAD) with bicyclic monoterpenes

Author(s) -

Adam Waldemar,

De Lucchi Ottorino,

Hill Karlheinz

Publication year - 1982

Publication title -

chemische berichte

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.667

H-Index - 136

eISSN - 1099-0682

pISSN - 0009-2940

DOI - 10.1002/cber.19821150527

Subject(s) - camphene , cycloaddition , bicyclic molecule , chemistry , cyclopropane , pinene , medicinal chemistry , steric effects , stereochemistry , organic chemistry , ring (chemistry) , catalysis , chromatography , essential oil

The cycloaddition of the bicyclic monoterpenes camphene ( 4 ), α‐pinene ( 5 ), β‐pinene ( 6 ), 2‐carene ( 7 ), bornene ( 8 ), and tricyclane 9 with PTAD was investigated. Only camphene and α‐pinene gave rearranged urazoles ( 11 , 14 ) via dipolar cycloaddition. Ene‐reaction was the predominant reaction course for α‐pinene (→ 15 ) and the exclusive route for β‐pinene (→ 16 ) and 2‐carene (→ 17 ). Steric hindrance by the gem ‐dimethyl group prevents cycloaddition of bornene. The cyclopropane rings in the tricyclane 9 and 2‐carene are not sufficiently strained to undergo [2π + 2σ]‐cycloaddition with PTAD. None of the monoterpenes gave [2π + 2σ]‐cycloaddition.

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