Khorop High School, Howrah, West Bengal, India Department of Chemistry, Taki Government College, North 24-Parganas-743 429, West Bengal, India Department of Chemistry, Organic Chemistry Section, Jadavpur University, Kolkata-700 032, India E-mail : sanjaybharin@yahoo.com, sanjay_bhar@chemistry.jdvu.ac.in Manuscript received 04 July 2013, accepted 05 July 2013 Dimethyl sulfoxide in combination with cyanuric chloride in dichloromethane solvent behaved differently with alcohols having different structural features. The products were obtained as methylene acetal or methyl thioether or methyl enethioether depending on the substitution pattern of the alcohols. A plausible mechanism has been proposed on the basis of isotope labeling studies.