Thermal rearrangement of {[2-(Arylmethylene)cyclopropyl]methyl}(phenyl)sulfanes and selanes.
{[2-(Arylmethylene)cyclopropyl]methyl}(phenyl)sulfanes and {[2-(arylmethylene)cyclopropyl]methyl}(phenyl)selanes, generated in situ from 2-(arylmethylene)cyclopropylcarbinols with sodium benzenethiolate and sodium benzeneselenolate, could undergo rearrangement upon heating to afford (2-arylmethylidenebut-3-enyl)(phenyl)sulfanes and (2-arylmethylidenebut-3-enyl)(phenyl)selanes, in good to excellent yields as mixtures of E- and Z-isomers, respectively. A radical rearrangement was proposed on the basis of control experiments for this process.
D005609:Free Radicals / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D012643:Selenium / Q000737:chemistry*; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D013696:Temperature
D005609:Free Radicals; D009942:Organometallic Compounds; D013438:Sulfhydryl Compounds; D012643:Selenium