97416-71-2Relevant academic research and scientific papers
Novel chemical behaviour of a [2,3] sigmatropic rearrangement product of 2-phenyltetrahydrothiopyranium 1-methylide
Doi, Satoshi,Shirai, Naohiro,Sato, Yoshiro
, p. 2181 - 2184 (2007/10/03)
1,3,4,5,6,11a-Hexahydro-7E-2-benzothionine 5, which is a [2,3] sigmatropic rearrangement product of 2-phenyltetrahydrothiopyranium 1-methylide 8, has been synthesized by reaction of 1-methyl-2-phenyltetrahydrothiopyranium triflate 3 with sodium amide in liquid ammonia or by the fluoride ion-induced desilylation of trans-2-phenyl-1-[(trimethylsilyl)methyl]tetrahydrothiopyranium perchlorate trans-7. Compound 5 is stable at room temperature and reverts to ylide 8 by ring-opening.
Regiochemistry and Stereochemistry of Nickel-Promoted, Carbon-Carbon Bond-Forming Reactions of Cyclic Sulfur Compounds
Tiecco, Marcello,Tingoli, Marco,Wenkert, Ernest
, p. 3828 - 3831 (2007/10/02)
Reaction of methylmagnesium iodide and phenylmagnesium bromide with thianaphthene, dibenzothiophenone, thianthrene, and 2,3-dihydrothiapyran in the presence of nickel dichloride have been shown to yield, regioselectively in most cases, ring-opened products in which the carbon-sulfur bonds have been replaced by carbon-carbon bonds.Stereospecific carbon-carbon bond formation has taken place in the reactions of thianaphthene and 2,3-dihydrothiapyran, the products having maintained the cis-olefin configuration of the starting sulfur compounds.Isomerization into the more stable compounds has been observed in some cases.
