A New Facile One-Pot Synthesis of Cyclopropyl Vinyl Sulfides

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• Results of DNOE experiments on (Z) and (E) diastereoisomers of 3g: Irradiation of the proton on the tertiary carbon of the C3 ring at δH = 1.95 had no effect on the signal of the vinyl proton at δH = 6.50. Irradiation of the analogous proton of the other isomer at δH = 1.60 produced an increase in the signal of the vinyl proton at δH = 6.25 of 6.7%. Hence the two protons with δH = 1.60 and 6.25 are cis to the double bond, i.e. the isomer is (Z). The signals at δH = 1.95 and 6.50 therefore correspond to the (E) isomer. Similarly, DNOE experiments enabled us to assign the signals of the cyclopropane protons of the two cis hydrogens and the two trans hydrogens in relation to the proton on the tertiary carbon of the C3 ring. The signals for the trans protons were shifted upfield; δH = 0.50 - 0.70 while those for the cis protons were shifted downfield; δH = 0.80 - 1.00.
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