87480-80-6Relevant academic research and scientific papers
Titanocene dichloride as a convenient catalyst for the diastereoselective oxidation of 2-substituted 1,3-dithianes and 1,3-dithiolanes
Della Sala, Giorgio,Labano, Stefania,Lattanzi, Alessandra,Tedesco, Consiglia,Scettri, Arrigo
, p. 505 - 510 (2002)
Cp2TiCl2 is an efficient catalyst for the diastereoselective mono-oxidation of 2-substituted 1,3-dithianes and 1,3-dithiolanes by tert-butyl hydroperoxide; comparable stereoselectivities and better yields than Ti(i-PrO)4 w
Diastereoselective Alkylation of Ketone Enolates using a 1,3-Dithiane 1-Oxide Auxiliary
Page, Philip C. Bulman,Slawin, Alexandra M. Z.,Westwood, Donald,Williams, David J.
, p. 185 - 187 (2007/10/02)
Acyldithiane 1-oxides readily undergo deprotonation to give chelated metal enolates which react with iodomethane to give alkylated products with good selectivity.
Structure and Absolute Stereochemistry of Thioacetal Sulphoxides Obtained by Fungal Metabolism of 2 Alkyl-1,3-Dithianes
Auret, Barbara J.,Boyd, Derek R.,Cassidy, E. Sally,Hamilton, Robert,Turley, Fiona,Drake, Alex F.
, p. 1547 - 1552 (2007/10/02)
Monosulphoxide metabolites of 2-methyl-, 2-t-butyl-, 2,2-dimethyl-, and 2-methyl-2-t-butyl-1,3-dithiane have been isolated after addition of the thioacetals to growing cultures of the fungi Aspergillus foetidus, Mortierella isabellina and a Helminthosporium species.The optical yields of the chiral monosulphoxide metabolites (0-72percent) were determined by n.m.r. analysis in (-)-phenyl- or 1-(+)-9-anthryl-2,2,2-trifluoroethanol-CDCl3 solvent mixtures.The signs of Cotton effects obtained from c.d. spectra have been used to assign the absolute stereochemistry of the chiral thioacetal sulphoxides.Optically pure samples 2,2-dimethyl-1,3-dithiane 1-oxide, cis-2-methyl-1,3-dithiane 1-oxide, and trans-2-methyl-1,3-dithiane 1-oxide, have been obtained by a chemical resolution method which provides confirmation of optical yields and absolute stereochemistry.The fungal metabolism results indicate that the mono-oxygenase enzymes can stereodifferentiate between prochiral (diastereotopic) Ione pairs on a sulphur atom and also between prochiral (enantiotopic) thioalkyl substituents on a carbon atom during the formation of monosulphoxides.
REGIOSELECTIVITY OF METALATION OF 1,3-DITHIOLANES AND 1,3-DITHIOLANE 1-OXIDES
Carey, Francis A.,Dailey, Oliver D.
, p. 169 - 174 (2007/10/02)
Deprotonation of 1,3-dithiolane 1-oxide (3) and tran-2-phenyl-1,3-dithiolane 1-oxide (5) leads to cleavage of the derived anions.Cleavage reactions do not occur with trans-hexahydro-1,3-benzodithiole (7), its 1-oxide, or its 1,1-dioxide all of which can b
