Tetrathiomolybdate mediated rearrangement of aziridinemethanol tosylates: a thia-aza-Payne rearrangement.
Aziridinemethanol sulfonate esters react with tetrathiomolybdate 1 to give thiirane derivatives as the major product and cyclic disulfides as minor product under mild reaction conditions via an unprecedented thia-aza-Payne-type rearrangement. Interestingly, when the reaction of 1 was carried out with 2-aziridino-cyclohexanol derivatives it resulted in the formation of thia-bicyclo[3.1.1]heptane or dithia-bicyclo[3.2.1]octane derivatives.
Sureshkumar
Devarajulu
D
Department of Organic Chemistry, Indian Institute of Science, Bangalore-560012, Karnataka, India.
Koutha
Srinivasamurthy
S
Ganesh
Venkataraman
V
Chandrasekaran
Srinivasan
S
D000438:Alcohols / Q000737:chemistry*; D001388:Aziridines / Q000737:chemistry*; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015394:Molecular Structure; D008982:Molybdenum / Q000737:chemistry*; D013237:Stereoisomerism; D013440:Sulfides / Q000138:chemical synthesis* / Q000737:chemistry; D014105:Tosyl Compounds / Q000737:chemistry*
D000438:Alcohols; D001388:Aziridines; D013440:Sulfides; D014105:Tosyl Compounds; D008982:Molybdenum; C020809:tetrathiomolybdate; C013523:ethylene sulfide