96793-90-7Relevant academic research and scientific papers
Sulfite formation versus chlorination of benzyl alcohols with thionyl chloride
Rodriguez, Deana A.,Priefer, Ronny
, p. 3045 - 3048 (2014/05/20)
Recently, we have reported the photolytic decay of a library of para-substituted dibenzylic sulfites in a Srinivasan-Griffin-Rayonet photochemical reactor. In an attempt to synthesize the complete library for that study we discovered that bis(p-methoxybenzyl) sulfite and bis(p-phenoxybenzyl) sulfite could not be formed and only their corresponding benzyl chlorides were synthesized. Thus, sulfite formation versus chlorination of a range of para-substituted benzyl alcohols with thionyl chloride was investigated. Sulfite formation was observed to be parabolically related to Swain and Lupton's Field ?-values while chloride formation was found to be linearly related to Swain and Lupton's Field ?-values.
Photolytic decomposition of dibenzylic sulfites
Grenga, Paolo N.,Stoutenburg, Eric G.,Priefer, Ronny
, p. 4933 - 4937 (2012/11/13)
The photolytic decay of a library of para-substituted dibenzylic sulfites has been evaluated by UV radiation in a Srinivasan-Griffin-Rayonet photochemical reactor in various deuterated solvents. The decay for each dibenzylic sulfite was examined with respect to Swain and Lupton's field constant, F. The rate of photolytic decay varies depending on the identity of the benzyl substituents. Furthermore, it has been observed that the solvent affects both the rate of sulfite photolytic decay as well as final product distribution.
Generalized synthesis and physical properties of dialkoxy disulfides
Zysman-Colman, Eli,Harpp, David N.
, p. 5964 - 5973 (2007/10/03)
A substrate study was undertaken in order to probe the scope of S 2Cl2 coupling of alcohols to form dialkoxy disulfides. Compounds 1b and If are new; along with 1a, 1c, 1h, and 1j, all of the title compounds are fully characterized, and the yields of 1a and 1c have been optimized from previously reported syntheses. The effect of the R-substituent about the OSSO moiety has been carefully probed as yields vary. A substrate and a solvent study of the coalescence behavior of this class was carried out. The origin of the inherently large barrier to rotation and the resultant thermal decomposition pathway is discussed. Both phenomena are shown to be solvent independent; hindered rotation is substrate independent. The decomposition of 1a is ca. 7 kcal/mol higher than the barrier to rotation about the S-S bond. The combined evidence suggests acyclic unsymmetric homolytic cleavage of the dialkoxy disulfide.
Preparation of 4-substitute benzyl sulfoxylates and related chemistry
Tardif, Sylvie L.,Harpp, David N.
, p. 4791 - 4795 (2007/10/03)
Preparation of dibenzyl sulfoxylate 7a and 4-substituted benzyl sulfoxylates (7b, 4-NO2; 7c, 4-Cl; 7d, 4-CH3O, 7e: 4-CH3) are reported. The unexpected stability of 7b has permitted the first X-ray determination at room tem
