407619-28-7Relevant academic research and scientific papers
Development of a novel benzyl mercaptan as a recyclable odorless substitute of hydrogen sulfide
Matoba, Manabu,Kajimoto, Tetsuya,Node, Manabu
, p. 1930 - 1934 (2008/03/27)
2,4,6-Trimethoxybenzyl mercaptan (4) was developed as an odorless substitute of hydrogen sulfide to afford β-mercapto carbonyl compounds in a Michael addition and to convert alkyl bromides into alkanethiols. Detrimethoxybenzylation of the Michael adducts prepared from 4 and α,β-unsaturated esters or ketones was facilely carried out by treatment with a solvent mixture of trifluoroacetic acid and toluene to give β-mercapto carbonyl compounds. Successive alkaline hydrolysis of 2,4,6-trimethoxybenzyl isothiouronium salt, which was obtained as a side product, regenerated 4 accompanying disulfide 8 in good yield. The disulfide 8 was also converted into 4 by reduction with LiAlH4. A similar protocol was applicable to the synthesis of alkanethiols using the S N2 reaction of alkyl bromides. Our method could be complementary to the classical method of using malodorous benzyl mercaptan as a nucleophile and Birch reduction for debenzylation. Georg Thieme Verlag Stuttgart.
Development of Odorless Thiols and Sulfides and Their Applications to Organic Synthesis
Nishide, Kiyoharu,Ohsugi, Shin-Ichi,Miyamoto, Tetsuo,Kumar, Kamal,Node, Manabu
, p. 189 - 200 (2007/10/03)
Development of new odorless thiols (dodecanethiol, 4-n- heptylphenylmethanethiol, 4-trimethylsilylphenylmethanethiol, 4-trimethylsilylbenzenethiol) and an odorless sulfide (1-methylsulfanyldodecane) and their applications to dealkylation, Michael addition, Swern oxidation, and Corey-Kim oxidation are described.
Odorless substitutes for foul-smelling thiols: Syntheses and applications
Node, Manabu,Kumar, Kamal,Nishide, Kiyoharu,Ohsugi, Shin-Ichi,Miyamoto, Tetsuo
, p. 9207 - 9210 (2007/10/03)
Several alkanethiols and p-alkylphenylmethanethiols were synthesized, and their odors were compared with those of ethanethiol and benzyl mercaptan by human and instrumental sensors. Among the various thiols analyzed, 1-dodecanethiol (1) and p-heptylphenylmethanethiol (3) were revealed to be odorless. 1-Dodecanethiol (1) has been used instead of ethanethiol for dealkylation of ethers, and p-heptylphenylmethanethiol (3) can replace benzyl mercaptan in the preparation of a 1,3-mercapto alcohol from an α,β-unsaturated ketone. These odorless thiols will greatly improve the physical environment of the researcher working with these foul-smelling compounds.
