Abstract
Triene-conjugated nitrile ylides of the types 18 and 20 with α,β aromatic and γ,δ; e,ζ olefinic unsaturation undergo intramolecular cyclisation on to the γ,δ bond via a formal 1,1-cycloaddition reaction to give respectively endo- and exo-1-alkenylcyclopropa[c]isoquinolines 23 and 25 as primary products. The endo-isomers 23 rearrange spontaneously at 0 °C to give 1,4-dihydro-1,4-prop[2]enoisoquinolines 24 via an aza-Cope reaction. The exo-isomers 25 give the same product on heating at 70 °C via equilibration with the endo form 26 as the primary step, provided that the concentration of the latter at equilibrium is not strongly disfavoured by the steric effect of substituents R1 and R2. If it is then an alternative rearrangement also occurs to give the azabenzo[3,4]barbaralane derivative 29.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callMore From: Journal of the Chemical Society, Perkin Transactions 1
Disclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
