80192-89-8Relevant 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.
A Ramberg-Baecklund route to the stilbenoid anti-cancer agents combretastatin A-4 and DMU-212
Robinson, James E.,Taylor, Richard J. K.
, p. 1617 - 1619 (2008/02/08)
A concise route to combretastatin A-4, a potent inhibitor of tubulin polymerisation, using a Ramberg-Baecklund reaction to form the key (Z)-stilbene unit has been developed; this Ramberg-Baecklund approach has also been extended to prepare the (E)-stilbene DMU-212, which also possesses interesting growth inhibitory properties. The Royal Society of Chemistry.
