Synthesis of 4,4-disubstituted-4H-benzo[d][1,3]oxathiin-2-ones, a new class of compounds
4,4-Dialkyl and 4,4-diaryl-4H-benzo[d][1,3]oxathiin-2-ones were synthesized by the reaction of 2-(mercapto-phenyl)-dialkyl- (or diaryl)-methanol with CDI in excellent yield. The 2-(mercaptophenyl)-dialkyl- (or diaryl)-methanols were prepared by the reaction of commercially available methylthiosalicylate with an ppropriate alkyl or aryl Grignard reagent. Copyright Taylor & Francis Group, LLC.
Kamila, Sukanta,Khan, Omair,Zhang, Hongming,Biehl, Edward R.
p. 1419 - 1429
(2007/10/03)
1,3-Oxathiane ring formation through intramolecular Pummerer reaction of alkyl ortho-hydroxymethylphenyl sulfoxides
The intramolecular Pummerer rearrangement of 2-(2-alkyl-sulfinylphenyl)- 2-propanols (1a, 1c-1g) yielded 1,3-oxathianes (2a, 2c-2g) in the presence of p-toluenesulfonic acid and molecular sieves 3A. Alkyl halides were converted into 1,3-oxathiane derivatives in three steps via this rearrangement.