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Paper | Regular issue | Vol 53, No. 4, 2000, pp.897-904
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8834
Easy Access to Medium Rings by Entropy/Strain Reduction, Part 4. A Simple and Mild Route to Some Substituted 2,7-Dihydro-1H -oxepins, thiepins and a Phosphepin

James G. Walsh and Declan G. Gilheany*

*Department of Chemistry, National University of Ireland, Maynooth, Co. Kildare, Ireland


Reaction of substituted 1,6-dibromohexa-2,4-dienes (3) with sulfide ion leads to the corresponding dihydro-1H-thiepins (5) which were characterised as their sulfones 6. Reaction of 3 with dichlorophenylphosphine in the presence of sodium gives a low yield of dihydro-1H-phosphepin oxide (7). Reaction of the 1,6-diols (2) with butyllithium and p-toluenesulfonyl chloride gives the dihydro-1H-oxepins (8).