Synthesis and Reactions of 1-Thianaphthalenes

概要

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Treatment of 1-methyl-4-phenyl-1-thio-2H-chromenium perchloarate (2) with sodium hydride yielded a dimeric compound 4 and two rearrangement products 5 and 6 via unstable 1-methyl-4-phenyl-1-thianaphthalene (3). On heating with potassium hydroxide in ethanol, 1-methyl-2,4-diphenyl-1-thio-2H-chromenium perchlorate(9) gave a dimeric compound 13 and two ring-opened products 11a and 12a, but no rearrangement product. On the other hand, 2-cyano-1-methyl-4-phenyl-1-thianaphthalene (20) prepared from the corresponding 1-thiochromenium salt 19 by treatment with triethylamine in ethanol was quite stable, and it is the first example of a stable and crystalline 1-thianaphthalene.Reactions of the 1-thianaphthalene 20 with electrophiles such as tetracyanoethylene, maleic anhydride, and 4-phenyl-1-thianaphthylium perchlorate gave the dimeric compound 23. However, the treatment of 20 with dimethyl acetylenedicarboxylate yielded a new ring expansion product 27 having a sulfur-containing nine-membered ring.
社団法人日本薬学会の論文
1988-10-25