Stereoselective reductions and alcohol deoxygenation by a phosphine in the 5,10-dihydrodibenzo[b,e]phosphorin series
- 1 January 1978
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 5,p. 465-468
- https://doi.org/10.1039/p19780000465
Abstract
The stereospecific reductions of the 5-methyldibenzo[b,e]phosphorin-10(5H)-one (4) by NaH2Al(OC2H4OMe)2 and LiHAl(OBut)3 give the pseudoaxial and pseudoequatorial alcohols (14) and (13), respectively. Alcohol (13), but not (14), undergoes ready oxygen transfer from carbon to phosphorus. LiAlH4 deoxygenates the pseudo-equatorial alcohol 5-methyl-5,10-dihydrodibenzo[b,e]phosphorin-10-ol 5-oxide (6), but not the corresponding pseudoaxial alcohol (7), to the phosphine oxide (8). Neither the isomeric alcohols (6) and (7) nor their acetate esters (17) and (18) equilibrate or isomerize under electron impact at 200 °C.Keywords
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