α-PHOSPHORYL SULFOXIDES 7.1CHIROPTICAL PROPERTIES OF α-PHOSPHORYL SULFOXIDES
- 1 March 1988
- journal article
- research article
- Published by Taylor & Francis in Phosphorus and Sulfur and the Related Elements
- Vol. 36 (1-2) , 79-84
- https://doi.org/10.1080/03086648808079001
Abstract
The paper describes the synthesis and chiroptical properties of (+)-α-phosphoryl sulfoxides of general formulae, R1 2P(X)CHR2S(O)Tol-p (where R1=MeO, EtO. Ph, Me2N, X=O,S, R2=H,Me, Cl) obtained from (-)-(S)-menthyl p-toluenesulfinate and the corresponding α-phosphonate, α-thiophosphonate and α-phosphinoxide anions. The CD curves of (+)-α-phosphoryl sulfoxides are of the same shape with two Cotton effects of opposite sign. At 240–245 nm one observes the positive Cotton effect while that at 220 nm is negative. The CD spectra of all (+)-α-phosphoryl sulfoxides measured are almost identical with that of (+)-(R)-methyl p-tolyl sulfoxide indicating that they have the S-chirality at sulfur. The change of ethanol for isooctane as a solvent does not influence the UV and CD spectra.Keywords
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