16621-37-7Relevant articles and documents
NaOH-promoted thiolysis of oxiranes using 2-[bis(alkylthio)methylene]-3- oxo-N-o-tolylbutanamides as odorless thiol equivalents
Yu, Haifeng,Dong, Dewen,Ouyang, Yan,Wang, Yan,Liu, Qun
, p. 151 - 155 (2008/03/13)
A convenient and efficient protocol for the thiolysis of oxiranes using 2-[bis(alkylthio)methylene]-3-oxo-N-o-tolylbutanamides as thiol equivalents has been developed. Promoted by sodium hydroxide (NaOH) in ethanol at room temperature, the cleavage commences and the generated thiolate anions undergo nucleophilic addition in situ. β-Hydroxy Sulfides were obtained in high yields along with good β-regioselectivity, and trans β-hydroxy Sulfides were also isolated. The thiolysis of one α,β-epoxyketone product with the thiol equivalents was accomplished to afford the corresponding α-carbonyl sulfides in excellent yields. In all the cases, 3-oxo-N-o-tolylbutanamide, the precursor of the thiol equivalents, could be recovered in the novel thiolysis process as a byproduct in good yield. Georg Thieme Verlag Stuttgart.
The Use of Proton-exchanged X-Type Zeolite in Catalysing Ring-opening Reactions of 2-Substituted Epoxides with Nucleophiles and its Effect on Regioselectivity
Takeuchi, Hiroshi,Kitajima, Kunio,Yamamoto, Yasuhiro,Mizuno, Kiyokazu
, p. 199 - 203 (2007/10/02)
The use of proton-exchanged X-type zeolite in catalysing ring-opening reactions of 2-alkyl substituted epoxides with nucleophiles gives a high regioselectivity and functional-selective catalysis giving allylic products from allylic nucleophiles.Mechanistic aspects are discussed.
SYNTHESIS OF 1,3,2-OXATHIAPHOSPHOLANE-2-SULFIDE DERIVATIVES
Comel, Alain,Kirsch, Gilbert,Paquer, Daniel
, p. 229 - 234 (2007/10/02)
5-Substituted 2-alkyl (or aryl, heteroaryl, ...)thio-1,3,2-oxathiaphospholane-2-sulfides 5 are readily accessible by reaction of the triethylammonium salt 1 of a diester of the phosphorotetrathioic acid with appropriate epoxides in the presence of BF3/Et2O as catalyst.Key words: BF3/Et2O; cyclisation reaction; NMR; oxathiaphospholane derivatives; oxiranes; phosphorotetrathioic acid; triethylammonium salts.
