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ortho-Alkenyl phenols react rapidly with PhSeCl to produce derivatives of 2,3-dihydrobenzofuran or 3,4dihydro-2H-benzo [blpyran (depending on the nature of the ortho-substituent) in a process shown to belong to the general class of cyclofunctionalisations.

Z,Z)-Cyclonona-1,5-diene reacts stereoselec-temp.) of (2; R = H) regenerates (70%) the origin a reaction product (2; R = Ac). Treatment of the alcohol (2; R = H) with Ph3SnH6 in refluxing PhMe gives the alcohol CYCLOFUNCTIONALISATION~ is an efficient route to hetero-(3) (90%) shown, by comparison with an authentic sample' cycles1, containing the synthetically useful benzeneseleno-and by comparison of the derived sharp-melting acid group3 [equation (l)] . We have found a transannular phthalates,' to have the structure and stereochemistry ,example of this process that demonstrates how it can be used tively with PhSeCl in AcOH to give (2; R = Ac). defined by (3) . § to make a C-C bond [equation ( l ) , X = C1.t 'CL'Under appropriate conditions the readily available4 diene (1) reacts with PhSeCl to give the substituted hydrindan '

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