Synthesis and Reactions of 1-Thianaphthalenes
Treatment of 1-methyl-4-phenyl-1-thio-2H-chromenium perchlorate (2) with sodium hydride yielded a dimeric compound 4 and two rearrangement products 5 and 6 via unstable 1-methy1-4-phenyl-l-thianaphthalene (3). On heating with potassium hydroxide in ethanol, 1-methy1-2, 4-dipheny1-1-thio-2H-chromeniu...
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| Published in | Chemical & pharmaceutical bulletin Vol. 36; no. 10; pp. 3816 - 3825 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
Tokyo
The Pharmaceutical Society of Japan
1988
公益社団法人日本薬学会 Maruzen Japan Science and Technology Agency |
| Subjects | |
| Online Access | Get full text |
| ISSN | 0009-2363 1347-5223 |
| DOI | 10.1248/cpb.36.3816 |
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| Abstract | Treatment of 1-methyl-4-phenyl-1-thio-2H-chromenium perchlorate (2) with sodium hydride yielded a dimeric compound 4 and two rearrangement products 5 and 6 via unstable 1-methy1-4-phenyl-l-thianaphthalene (3). On heating with potassium hydroxide in ethanol, 1-methy1-2, 4-dipheny1-1-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-l-methy1-4-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. |
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| AbstractList | Treatment of 1-methyl-4-phenyl-1-thio-2H-chromenium perchlorate (2) with sodium hydride yielded a dimeric compound 4 and two rearrangement products 5 and 6 via unstable 1-methy1-4-phenyl-l-thianaphthalene (3). On heating with potassium hydroxide in ethanol, 1-methy1-2, 4-dipheny1-1-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-l-methy1-4-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. 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. |
| Author | AOKI, HARUMI HORI, MIKIO SHIMIZU, HIROSHI KATAOKA, TADASHI |
| Author_FL | AOKI HARUMI SHIMIZU HIROSHI HORI MIKIO KATAOKA TADASHI |
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| Keywords | Chemical rearrangement Sulfur heterocycle Base catalysis Potassium Hydroxides Bicyclic compound Aromatic compound Electrophilic reaction Sodium Hydrides Dimerization Scission Ring expansion Ylide |
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| References | c) M. Hori, T. Kataoka, H. Shimizu, and S. Ohno, and K. Narita, Tetrahedron Lett, J. Org. Chem., 45, 2468 (1980). 9) G. Suld and C. C. Price, J. Am. Chem. Soc., 84, 2090 (1962). 5) A. G. Hortmann, R. L. Harris, and J. A. Miles, J. Am. Chem. Soc., 96, 6119 (1974). c) M. Hori, T. Kataoka, H. Shimizu, S. Ohno, K. Narita, and H. Koyama, J. Chem. Soc., Chem. Commun., 1981, 364. b) M. Hori, T. Kataoka, H. Shimizu, S. Ohno, K. Narita, H. Takayanagi, H. Ogura, and Y. litaka, Tetrahedron Lett., 1979, 4315. 6) A. Lüttringhaus, N. Engelhard, and A. Kolb, Justus Liebigs Ann. Chem., 654, 189 (1962). 3) a) M. Hori, T. Kataoka, H. Shimizu, and O. Komatsu, J. Chem. Soc., Chem. Commun., 1985, 883. b) M. Hori, T. Kataoka, H. Shimizu, O. Komatsu, and K. Hamada, J. Org. Chem., 52, 3668 (1987). 1) a) M. Hori, T. Kataoka, H. Shimizu, K. Narita, S. Ohno, and H. Aoki, Chemistry Lett., 1974, 1101. 2) a) M. Hori, T. Kataoka, H. Shimizu, S. Ohno, and K. Narita, Tetrahedron Lett., 1978, 251. b) M. Hori, T. Kataoka, H. Shimizu, and S. Ohno, and K. Narita, Tetrahedron Lett., 1978, 255. d) S. Ohno, H. Shimizu, T. Kataoka, and M. Hori, Tetrahedron Lett, J. Org. Chem., 49, 2472 (1984). 8) W. T. Flowers, G. Holt, and M. A. Hope, J. Chem. Soc., Perkin Trans. 1, 1974, 1116. 7) B. Angelo, Bull. Soc. Chim. Fr., 5, 1710 (1969). 4) For a preliminary communication of a portion of this work, see: M. Hori, T. Kataoka, H. Shimizu, and H. Aoki, Heterocycles, 5, 413 (1976). |
| References_xml | – reference: 2) a) M. Hori, T. Kataoka, H. Shimizu, S. Ohno, and K. Narita, Tetrahedron Lett., 1978, 251. – reference: d) S. Ohno, H. Shimizu, T. Kataoka, and M. Hori, Tetrahedron Lett, J. Org. Chem., 49, 2472 (1984). – reference: 6) A. Lüttringhaus, N. Engelhard, and A. Kolb, Justus Liebigs Ann. Chem., 654, 189 (1962). – reference: c) M. Hori, T. Kataoka, H. Shimizu, and S. Ohno, and K. Narita, Tetrahedron Lett, J. Org. Chem., 45, 2468 (1980). – reference: 3) a) M. Hori, T. Kataoka, H. Shimizu, and O. Komatsu, J. Chem. Soc., Chem. Commun., 1985, 883. – reference: 5) A. G. Hortmann, R. L. Harris, and J. A. Miles, J. Am. Chem. Soc., 96, 6119 (1974). – reference: 7) B. Angelo, Bull. Soc. Chim. Fr., 5, 1710 (1969). – reference: 8) W. T. Flowers, G. Holt, and M. A. Hope, J. Chem. Soc., Perkin Trans. 1, 1974, 1116. – reference: 4) For a preliminary communication of a portion of this work, see: M. Hori, T. Kataoka, H. Shimizu, and H. Aoki, Heterocycles, 5, 413 (1976). – reference: 9) G. Suld and C. C. Price, J. Am. Chem. Soc., 84, 2090 (1962). – reference: b) M. Hori, T. Kataoka, H. Shimizu, and S. Ohno, and K. Narita, Tetrahedron Lett., 1978, 255. – reference: b) M. Hori, T. Kataoka, H. Shimizu, S. Ohno, K. Narita, H. Takayanagi, H. Ogura, and Y. litaka, Tetrahedron Lett., 1979, 4315. – reference: c) M. Hori, T. Kataoka, H. Shimizu, S. Ohno, K. Narita, and H. Koyama, J. Chem. Soc., Chem. Commun., 1981, 364. – reference: 1) a) M. Hori, T. Kataoka, H. Shimizu, K. Narita, S. Ohno, and H. Aoki, Chemistry Lett., 1974, 1101. – reference: b) M. Hori, T. Kataoka, H. Shimizu, O. Komatsu, and K. Hamada, J. Org. Chem., 52, 3668 (1987). |
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| Snippet | Treatment of 1-methyl-4-phenyl-1-thio-2H-chromenium perchlorate (2) with sodium hydride yielded a dimeric compound 4 and two rearrangement products 5 and 6 via... 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... |
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| SubjectTerms | 1, 2-rear-rangement 1, 2-rearrangement 1, 4-rearrangement 1-thianaphthalene Chemistry cyclic sulfur ylide dimerization electophile electrophile Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Organic chemistry Preparations and properties ring expansion thiabenzene |
| Title | Synthesis and Reactions of 1-Thianaphthalenes |
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