3-exo,3′-exo-(1R,1′R)-Bithiocamphor — a versatile source for functionally different 3,3′-bibornane derivatives, II. 1 An access to 3-exo,3′-exo-(1r,1′r)-bicamphor and related compounds |
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Authors: | Werner Schroth Ekkehard Hintzsche Roland Spitzner Dieter Str hl Katrin Schmei Joachim Sieler |
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Affiliation: | aInstitut für Organische Chemie der Martin-Luther-Universität Halle-Wittenberg, Weinbergweg 16, D-06099 Halle (Saale), USA bInstitut für Anorganische Chemie der Universität Leipzig, Linnéstraβe 3, D-04103 Leipzig, USA |
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Abstract: | 3-exo,3′-exo-(1R,1′R)-bicamphor (12) is obtained from 3-exo,3′-exo-(1R,1′R)-bithtiocamphor (3) by condensation with hydrazine hydrate followed by hydrolysis of the resulting dihydropyridazine 11. Deprotonation of 12 with NaH and subsequent treatment with potassium hexacyanoferrate (III) furnishes the 2,2′-dioxo-3,3′-bibornanylidene 13, whilst reduction of 12 with L1AlH4 affords the 3,3′-biisoborneol 16. Further related transformations to various 2,2′-difunctional 3,3′-bibornane derivatives are described, which are could be of interest as chiral ligands |
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