Cycloadditions of diphenylnitrilimine with tropone and with tricarbonyltroponeiron. Thermal [1,5] sigmatropic rearrangements of the [π6s+π4s] cycloadducts of 1,3-dipoles with tropone
- 1 January 1977
- journal article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 8,p. 939-944
- https://doi.org/10.1039/p19770000939
Abstract
The reaction of diphenylnitrilimine (benzonitrile N-phenylimide) with tropone has been reinvestigated and eight products have been detected. In addition to the [π6s+π4s] cycloadduct formed by reaction at positions 2 and 7 of tropone, both the regioisomeric [π2s+π4s] adducts involving positions 2 and 3 and positions 4 and 5 were obtained. The reaction of tricarbonyltroponeiron, which was more reactive than tropone itself, gave a mixture of two regioisomers. The specific [1,5] sigmatropic rearrangement of the [6 + 4] cycloadducts of diphenylnitrilimine and benzonitrile oxide with tropone, which involves selectively the sp2 carbon atom instead of either the oxygen or the nitrogen atom of the 1,3-dipole have been also studied.Keywords
This publication has 0 references indexed in Scilit: