3,3-Diaryl-3H-2,1-benzoxathiole 1-oxides: new sultine colour-formers for carbonless imaging

Abstract

Lithiations ofN-phenylbenzenesulfinamides followed by treatment with Michler’s ketone and subsequent cyclizations during acidic workup provide 3,3-diaryl-3H-2,1-benzoxathiole 1-oxides in reasonable to good yields. The title compounds 11a, c–e, h develop dark-blue colours in acidic media.

References

1. H. W. Gschwend and H. R. Rodriguez, Org. React., 1979, 26, 1.
2. N. S. Narasimhan and R. S. Mali, Synthesis, 1983, 957.
3. S. Matsui, A. Uejima, Y. Suzuki and K. Tanaka, J. Chem. Soc., Perkin Trans. 1, 1993, 701.
4. J. J. Fitt and H. W. Gschwend, J. Org. Chem., 1976, 41, 4029.
5. N. S. Narasimhan and B. H. Bhide, Tetrahedron, 1971, 27, 6171.
6. W. H. Puterbaugh and C. R. Hauser, J. Org. Chem., 1964, 29, 853.
7. J. Epsztajn, Z. Berski, J. Z. Brzezinski and A. Jozwiak, Tetrahedron Lett., 1980, 21, 4739.
8. R. S. Mali and S. N. Yeola, Synthesis, 1986, 755.
9. F. M. Hauser and D. Mal, J. Am. Chem. Soc., 1984, 106, 1098.
10. O. O. Mamaeva, F. M. Stoyanovich and M. M. Krayushkin, Izv. Akad. Nauk SSSR, Ser. Khim., 1991, 10, 2383(Russ), Chem. Abstr., 1992, 116, 6451h.
11. A. R. Katritzky and P. Lue, J. Org. Chem., 1990, 55, 74.
12. K. Iwakura, M. Sano and H. Kawasaki, JP 61,215,085, 1986; Chem. Abstr., 1987, 107, 68253t.
13. Y. Fujino, H. Kawai and K. Tsunemitsu, EP 291,600, 1988; Chem. Abstr., 1989, 110, 135074n.
14. R. W. Brunea and J. M. Raby, EP 201, 225, 1986; Chem. Abstr., 1985, 107, 87268t.
15. H. A. Selling and H. J. Mak, Synth. Commun., 1976, 6, 129.
16. F. W. Billmeyer, Jr. and M. Saltzman, Principles of Color Thechnology, Wiley, New York; ch. 2 and 3.