24979-69-9Relevant articles and documents
Synthesis of tsetse fly attractants from a cashew nut shell extract by isomerising metathesis
Baader,Podsiadly,Cole-Hamilton,Goossen
, p. 4885 - 4890 (2014)
Starting from a purified cashew nut shell extract containing mostly anacardic acid derivatives, the tsetse fly attractants 3-ethyl- and 3-propylphenol were selectively synthesised. The mixture was first converted into 3-(non-8-enyl)phenol in 98% purity via ethenolysis and distillation with concomitant decarboxylation. The olefinic side chain was then shortened by isomerising cross-metathesis with short-chain olefins in the presence of a [Pd(μ-Br)(tBu3P)]2 isomerisation catalyst and a second-generation Hoveyda-Grubbs catalyst, and the synthesis was completed by a hydrogenation step.
Acid-catalysed Aromatisation of Benzene cis-1,2-dihydrodiols: a Carbocation Transition State poorly stabilised by Resonance
Boyd, Derek R.,Blacker, John,Byrne, Briege,Dalton, Howard,Hand, Mark V.,et al.
, p. 313 - 314 (2007/10/02)
Acid-catalysed dehydration of 3-substituted benzene cis-1,2-dihydrodiols exhibits a Hammett plot with ρ=-8.2, consistent with reaction via a benzenonium ion-like intermediate; however, correlation of +M resonance substituents such as Me and MeO by ?p rather than ?+ constants indicates a marked imbalance between resonance and inductive stabilisation of the transition state.
