R. Livingstone
1964
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Abstract
Publisher Summary This chapter focuses on six-membered ring compounds of one hetero atom with different analogues. The thiopyrans thiins are the sulfur analogues of pyrans where the oxygen of the latter being replaced by sulfur. The structure of 3-benzyl-2,6-diphenyl-2H-thiopyran-5-carbaldehyde obtained by treating benzaldehyde with sodium polysulfide in boiling aqueous ethanol, has been solved by an X-ray diffraction study. Thiopyranyl 1,1-dioxide anions, thiinyl 1,1-dioxide anions have been obtained by treating the appropriate thiopyran with sodium dimsyl in dimethyl sulfoxide. The 2H-benzor[b]thiopyrans, benzo[b]thiins, 2H-thiochromenes are obtained from the thiochroman-4-ols by distillation with phosphorus pentoxide, or by heating with freshly fused potassium hydrogen sulfate and then distilling. lsothiochromene, 1H-benzo[c]thiopyran is an unstable substance with an odor of naphthalene and it is obtained by heating isothiochroman-4-ol with potassium hydrogen sulfate. The sulfur analogue of xanthene is thioxanthene, which is prepared by the pyrolysis of phenyl o-tolyl sulfide or preferably by reducing thioxanthone by phosphorus and iodine, lithium tetrahydridoaluminate, sodium tetrahydridoborate in 95 0 ethanol. The earlier method of preparing silacyclohexanes involved adding silicon tetrachloride to pentane-l,5-dimagnesium dibromide in ether giving 1,1-dichioro-1-silacyclohexane, which was then alkylated by a Grignard reagent.