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Synthesis and Stereochemistry of Saturated and Partially Saturated 4-Aryl-4H-3,1-benzothiazine-2(1H)-thiones

✍ Scribed by Perjési, Pál ;Földesi, András ;Batta, Gyula ;Tamás, József

Publisher: Wiley (John Wiley & Sons)
Year: 1989
Tongue: English
Weight: 523 KB
Volume: 122
Category: Article
ISSN: 0009-2940
DOI: 10.1002/cber.19891220411

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✦ Synopsis

The reaction of 2-arylidenecyclohexanones 1 with dithiocarbamic acid gave three of the four possible diastereomers of 4-aryl-4a,5,6,7,8,8a-hexahydro-8a-hydroxy-4H-3,1-benzothiazine-2( 1 H)thiones 2-4. The isomeric composition of the reaction products was found to depend on the quantity of hydrochloric acid used as catalyst. 'H-NMR studies showed that the preferred conformation of the cis isomers 2 and 4 is controlled by the bulky 4aryl group, which always occupies the energetically more favourable quasiequatorial position. Dehydration of 2 -4 afforded ' 3 '53) S. Patai, The Chemistry o Alkenes, Chapter 2, Interscience 16) M. Karplus,

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