Abstract
In acetylation and formylation of phenoxathiin, besides 2-acyl-substituted main products, the 3-isomers form in ca. 10% yield. The structure of 3-acetylphenoxathiin isolated by fractional crystallization from the mixture resulted after acetylation was proved by means of physical and chemical methods.
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G. Vasiliu and O. Maior, Anal. Univ. Buc.,13, No. 1, 103 (1964).
O. Maior and M. Stanciu, Rev. Chim. (Buc.),20, 529 (1969).
D. Zavoianlc and O. Maior, Rev. Chim. (Buc.),21, 393 (1970).
O. Maior and A. Gioccba, Anal. Univ. Buc.,22, No. 1, 47 (1973).
G. Vasiliu, O. Maior, and I. Baciu, Anal. Univ. Buc.,12, 39 (1963).
R. G. Flowers and L. Flowers, J. Am. Chem. Soc.,71, 3102 (1949).
J. F. Nobis, A. J. Blardinelli, and D. J. Blaney, J. Am. Chem. Soc.,75, 3384 (1953).
E. Lescot, Ph. Buu-Hol Ng, and N. D. Xuong, J. Chem. Soc., 2408 (1956).
C. M. Suter, J. P. McKenzie, and C. E. Maxwell, J. Am. Chem. Soc.,58, 717 (1936).
W. I. Berg, O. Stapf, H. G. Schwabe, and K. Sandmau, Germ Pat. 234,800 (1974).
W. I. Berg, O. Stapf, H. G. Schwabe, and K. Sandmau, Germ. Pat. 2,325,300 (1973).
J. P. Coic and G. Saint-Ruf, J. Heterocycl. Chem.,15, 769 (1978).
M. Tonvita, J. Pharm. Soc. Jpn.,58, 510 (1938).
S. Florea, H. O. Kulinowski, O. Maior, and D. Gavriliu, Polish J. Chem.,70, 36 (1996).
D. Gavriliu and O. Maior, Anal. Univ. Craiova (Chimie),I, 103 (1995).
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Faculty of Chemistry, Organic Chemistry Department, University of Bucharest, 90-92 Panduri Road, Romania. SINDAN S.R.L. 11 1 Mai Blv., Bucharest, Romania.Published in Khlmiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1261–1265, September, 1996. Original article submitted May 8, 1996; revision submitted July 30, 1996.
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Maior, O., Stoicescu, D. & Gavriliu, D. Orientation effects in phenoxathiin acetylation and formylation. Chem Heterocycl Compd 32, 1084–1088 (1996). https://doi.org/10.1007/BF01164717
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DOI: https://doi.org/10.1007/BF01164717