79143-98-9Relevant academic research and scientific papers
SYNTHESIS OF 2-HETEROSUBSTITUTED 1,3-OXATHIANES AND THEIR REACTION WITH sec-BUTILLITHIUM
Fuji, Kaoru,Ueda, Masaru,Sumi, Kenzo,Fujita, Eiichi
, p. 2005 - 2009 (1981)
A series of 2-heterosubstituted 1,3-oxathianes were synthesized and their reactivity toward a strong base, sec-butyllithium, was studied.It was shown that sec-butyllithium attacked 2-heterosubstituted 1,3-oxathianes in three different ways depending upon the heteroatom at C-2; the removal of the proton at C-2, the nucleophilic attack at heteroatom, or the nucleophilic attack at C-2 took place.
Chemistry of 1,3-Oxathianes. Synthesis and Conformation of 2-Substituted 1,3-Oxathianes
Fuji, Kaoru,Ueda, Masaru,Sumi, Kenzo,Kajiwara, Kanji,Fujita, Eiichi,et al.
, p. 657 - 661 (2007/10/02)
The reaction of 2-lithio-1,3-oxathiane with a variety of electrophiles including alkyl halides and carbonyl compounds affords substitution and addition products, respectively.Alkyl metal halides such as (CH3)3SiCl, (CH3)3GeCl, and (CH3)3SnCl, or alkyl metal acetate, (CH3)3PbOAc, reacted with 1,3-oxathianyl anion to give rise to the corresponding 2-(group 14)-substituted 1,3-oxathianes (4). 2-(Methylthio)- and 2-(methylseleno)-1,3-oxathianes (6b and 6c) were prepared by a similar reaction of the anion with dimethyl disulfide and dimethyl diselenide, respectively.Other1,3-oxathianes substituted with a 2-methoxy or 2-dimethylamino group at C-2 have been synthesized to investigate the orientation of heteroatoms.Examination of their 1H and 13C NMR spectra leads to the conclusion that group 14 metals and a dimethylamino group occupy the equatorial position, while methoxy and methylthio groups favor the axial disposition due to the anomeric effect.Conclusive evidence was not obtained from the available data to decide whether 2-(methylseleno)-1,3-oxathiane (6c) exhibits the anomeric effect or not.
