158267-64-2

Upstream product

• 589-18-4 4-Methylbenzyl alcohol 

Downstream Products

• 589-18-4 4-Methylbenzyl alcohol 
• 104-87-0 4-methyl-benzaldehyde 

Relevant academic research and scientific papers

Chemical shift and coupling constant analysis of dibenzyloxy disulfides

Dialkoxy disulfides have found applications in the realm of organic synthesis as an S2 or alkoxy donor, under thermal and photolytic decompositions conditions, respectively. Spectrally, dibenzyloxy disulfides possess an ABq in the 1H NMR, which can shift by over 1.1 ppm depending on the substituents present on the aromatic ring, as well as the solvent employed. The effect of the said substituents and solvent were analyzed and compared to the center of the ABq, geminal coupling, and the differences in chemical shifts of the individual doublets. Additionally, quantum-chemical calculations demonstrated the intramolecular H-bonding arrangement, found within the dibenzyloxy disulfides.

Thermochemical properties of dibenzyloxy disulfides

The in situ thermal behavior of dialkoxy disulfides (OSSO) has been previously explored, however their neat thermal stability has yet to be examined. We synthesized a library of ten dibenzyloxy disulfide derivatives with various para-substituents. Each derivative was analyzed by TGA and DSC to discern molecular fragmentation. A correlation of the pattern of fragmentation to Swain and Lupton's R-value was observed. Also, DSC analysis revealed that when the para-substituent was a phenyl (i.e. bis(p-phenylbenzyloxy) disulfide), and successive runs were performed, the thermogram showed the presence of the fragmentation, and upon 1H NMR analysis its corresponding alcohol and aldehyde were observed.

Photolytic, autocatalyzed decomposition of benzylic dialkoxy disulfides

The dialkoxy disulfide moiety has been shown to go through an intramolecular fragmentation to liberate trappable S2, and can yield an alkoxy radical under photolytic conditions. We have examined a family of benzylic dialkoxy disulfides (X-Ph-CH2-O-S-S-O-CH2-Ph-X) under photolytic conditions and observed a correlation of decomposition based upon the substituent. We have been able to show that the decomposition is autocatalyzed and has a parabolic correlation with Swain and Lupton's field constant, F.

Thermolytic decomposition of benzylic dialkoxy disulfides

Dialkoxy disulfides have been used as an alkoxy radical source under photolytic conditions. In addition, this class of disulfide thermally decomposes to deliver S2 to dienes. We examined benzylic dialkoxy disulfides (X-Ph-CH2-O-S-S-O-CH2-Ph-X) under thermolytic conditions and observed that the rates of decomposition are related to Swain and Lupton's field constant, F. In addition, the observed non 1:1 ratio of alcohol to aldehyde reaffirms Harpp's-postulated cage mechanism. We have shown that the ratio is dependant upon the substituent present which can enhance the pi-stacking ability with the solvent, and thus favor diffusion out of the solvation cage yielding the non 1:1 ratio observed.

Preparation of 4-substitute benzyl sulfoxylates and related chemistry

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

Alkoxy disulfides as antimicrobial agents

Disclosed is a method of inhibiting the growth of microorganisms in, at, or on a locus subject to microbial attack, comprising introducing to said locus an antimicrobially effective amount of at least one alkoxy disulfide of formula:R-CHR-O-S-S-O-CHR-R wh

Recent chemistry of the chalcogen diatomics

The chemistry of the generation and trapping of diatomic sulfur (S2) and sulfur monoxide (SO) are reviewed with special emphasis on recent work, including initial efforts to detect and trap diatomic selenium (Se2).