DIASTEREOSELECTIVE SYNTHESIS AND STEREOCHEMISTRY OF (Z)-1-[3-ARYL-2-(PHENYLSULFANYL)-2-OXIRANYL]-1-ETHANONES

Abstract

Diastereoselective synthesis of a series of (Z)-1-[3-aryl-2-(phenylsulfanyl)-2-oxiranyl]-1-ethanones was effected from the reaction of (Z)-4-aryl-3-(phenylsulfanyl)-3-buten-2-ones with alkaline hydrogen peroxide in tetrahydrofuran. The stereochemistry of the oxiranes has been deduced from two-dimensional NOESY spectrum.

Keywords:

• 1-[3-aryl-2-(phenylsulfanyl)-2-oxiranyl]-1-ethanones
• hydrogen peroxide
• NMR
• synthesis
• stereochemistry
• (Z)-4-aryl-3-(phenylsulfanyl)-3-buten-2-ones

ACKNOWLEDGEMENT

S. Perumal thanks the CSIR and DST, New Delhi for major research projects. (S. Perumal and S. Selvaraj) thank DST for funds under IRHPA program for the purchase of a high-resolution NMR spectrometer and UGC for a major research project and funds under the DRS and ASIST programs.

Notes

^a Melting points not reported because all the compounds are semisolids except for (e) m.p. 58°C (lit. ⁷ 56–60°C).

^b Known compounds.

^a Melting points not reported as all the products are semisolids.

^b In these cases, retro-aldol condensation took place affording the corresponding benzaldehydes and 1-(phenylsulfanyl)acetone.