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- W2037381540 abstract "* To receive any correspondence. E-mail: RAVIN-SS@pelican.vista.ac.za Chiral auxiliaries consisting of functionalised camphor skeleta have proven to be highly versatile in asymmetric reactions.1,2 They are suitable for the design of conformationally rigid derivatives and are readily available. However, chiral auxiliaries containing more than one camphor skeleton are rare.12 We wish to report the synthesis and structure of a novel thioacetal 4 comprising of two camphor skeleta. 10-Mercaptoiso-borneol 213 was synthesised by reducing camphor-10sulphonyl chloride 114 with LAH. The required exo alcohol, 10-mercapto-iso-borneol 2, was separated from the endo isomer 3 by column chromatography and characterised by NMR spectroscopy. The acetal 4 was prepared by treating compound 2 with camphorquinone followed by subsequent purification of the compound by column chromatography. The structure was elucidated by NMR spectroscopy and confirmed by X-ray crystallography (Fig. 3). It has been observed15 that treatment of camphorquinone with diols, results in formation of acetals at both C-3 and C-2 positions. In this case, the C-2 position is more hindered and the thioacetalisation occurred exclusively at the C-3 position. The regioselectivity of the reaction was determined from the NMR experiments. X-ray diffraction analysis of compound 4 was undertaken so that the stereochemistry of the product could be established. The molecular structure and absolute configuration of compound 4 is shown in Fig. 3. The structure reveals that the sulfur atom is located at the exo position and the oxygen atom at the endo position of the thioacetal moiety. The two bornane skeleta J. Chem. Research (S), 2001, 405–407 J. Chem. Research (M), 2001, 1056–1069 Synthesis and crystal structure of a novel camphor based thioacetal Swarnam S Ravindrana*, Neliswa Skitia, Cedric McClelandb, Benita Bartonc and John Bacsad* aDepartment of Chemistry, Vista University, Private Bag X613, Port Elizabeth,6000, South Africa bDepartment of Chemistry, University of Port Elizabeth, Post Box 1600, Port Elizabeth, 6000, South Africa cCatalysis Research Unit, Faculty of Applied Science, Port Elizabeth Technikon, Private Bag X6011, Port Elizabeth, 6000, South Africa d*Department of Chemistry, University of Cape Town, Rondebosch, Cape Town, South Africa" @default.
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- W2037381540 date "2010-05-22" @default.
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- W2037381540 title "ChemInform Abstract: Synthesis and Crystal Structure of a Novel Camphor Based Thioacetal." @default.
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- W2037381540 doi "https://doi.org/10.1002/chin.200208194" @default.
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