5849-23-0

Basic information

• Product Name: 2-(diphenylhydroxymethyl)-1,3-dithiane
• Synonyms: 2-(diphenylhydroxymethyl)-1,3-dithiane
• CAS NO: 5849-23-0
• Molecular Weight: 302.461
• Mol File: 5849-23-0.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2-(diphenylhydroxymethyl)-1,3-dithiane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(diphenylhydroxymethyl)-1,3-dithiane(5849-23-0)
• EPA Substance Registry System: 2-(diphenylhydroxymethyl)-1,3-dithiane(5849-23-0)

Safety Data

• Hazardous Substances Data: 5849-23-0(Hazardous Substances Data)

Upstream product

• 505-23-7 1,3 dithiane 
• 119-61-9 benzophenone 

Downstream Products

• 4746-86-5 hydroxy-diphenyl-acetaldehyde 
• 1231151-35-1 3-[(2,2-diphenylvinyl)sulfanyl]propane-1-thiol 

Relevant articles and documents

An efficient photo-SET-induced cleavage of dithiane-carbonyl adducts and its relevance to the development of photoremovable protecting groups for ketones and aldehydes

Irradiation of dithiane-aldehyde/ketone adducts in the presence of benzophenone leads to C-C bond cleavage regenerating the carbonyl compounds. It is established that the mechanism of this reaction involves photochemically induced single electron transfer from the dithiane moiety to the excited molecule of ET-photosensitizer, accompanied by mesolytic C-C cleavage in the generated cation-radical, which is assisted by the anion- radical of benzophenone. This mechanism is confirmed by a Hammett plot study of the cleavage in the dithiane adducts of substituted aromatic aldehydes and a deuterium kinetic isotope effect study. Ab initio computations at UHF/6- 31G* and MP2/6-31G* levels of theory in conjunction with self-consistent reaction field (self-consistent isodensity-polarized continuum model), to account for the solvent effect, also support the experimental findings. The reaction is most efficient for protection of aromatic aldehydes and ketones and aliphatic ketones, and is a novel method for protecting carbonyl functionalities with a photoremovable group.

Acid-induced rearrangement reactions of -hydroxy-1,3-dithianes

Secondary benzylic or aliphatic -hydroxydithianes 1a-c rearrange to -thioketones when treated with acid. Related tertiary alcohols 1d-g eliminate to dithioketene ketals (e.g., 2d), which are ring-opened to thiols in some cases (1e, 1f). Allylic -hydroxydi

Asymmetric oxidation of 1,3-dithianes to 1,3-dithiane 1-oxides

Oxidation of 2-(1-hydroxy-1-methylethyl)-1,3-dithiane with the Sharpless reagent has been examined under various reaction conditions. Oxidation of 2-(1-hydroxy-1-methylethyl)-1,3-dithiane with Ti(OPri)4-diethyl L-(+)-tartrate-tert-bu