10-Oxo-10H-5λ 4, 10λ 4-thianthren-5-ylideneamine as a probe for stereochemistry in the formation and amination of fluoro-λ 6-sulfanenitriles

…, T Takano, S Asai, H Morita, M Hirata, T Yoshimura

Index: Fujii, Takayoshi; Takano, Tomoyoshi; Asai, Shinsuke; Morita, Hiroyuki; Hirata, Mitsuo; Yoshimura, Toshiaki Tetrahedron, 2006 , vol. 62, # 41 p. 9622 - 9627

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Citation Number: 3

Abstract

The fluorination of 10-oxo-10H-5λ4, 10λ4-thianthren-5-ylideneamine (2) with Selectfluor™ affords 5-fluoro-10-oxo-5, 10-dihydro-5λ6, 10λ4-thianthren-5-nitrile (4). The amination of 4 with morpholine gives 5-morpholino-10-oxo-5, 10-dihydro-5λ6, 10λ4-thianthren-5-nitrile (5). The stereochemical course of both reactions has been studied, while the configurations of their products, cis-isomer 4 and trans-5-morpholino-10-oxo-5, 10-dihydro-5λ6, 10λ4- ...