engleski

Excited state reactions of β-pyridyl-o-divinylbenzenes as a pathway to versatile polycyclic compounds with the unusual entrapment of multiple isomerized dihydro-intermediates

New hetero-stilbene derivatives, namely cis/trans-2/3/4-(2-vinylstyryl)pyridines, have been synthesized by Wittig reaction from the diphosphonium salt of α, α′-o-xylenedibromide, formaldehyde and 2/3/4-pyridinecarbaldehydes. The 2/3/4-(2-vinylstyryl)pyridines afforded, by photochemical intramolecular cycloaddition and cyclization reactions, diverse new polycyclic products with the pyridine ring integrated into the polycyclic skeletons. All of the new benzobicyclo[3.2.1]octadiene, benzobicyclo[2.1.1]hexene and vinyl- benzoquinoline products were identified and characterized by spectroscopic methods. Isomerized dihydro- intermediates *Revised Manuscript Click here to view linked References 2 (DHQs), that formed as a result of [1, n-H] shifts were also isolated, identified and characterized. DHQ intermediate isomers were never isolated in these conditions before.

styryl-pyridines ; photochemistry ; dihydro-intermediates

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