3-EXO,3'-EXO-(1R,1'R)-BITHIOCAMPHOR - A VERSATILE SOURCE FOR FUNCTIONALLY DIFFERENT 3,3'-BIBORNANE DERIVATIVES .2. AN ACCESS TO 3-EXO,3'-EXO-(1R,1'R)-BICAMPHOR AND RELATED-COMPOUNDS

Authors
SCHROTH W HINTZSCHE E SPITZNER R STROHL D SCHMEISS K SIELER J
Citation
W. Schroth et al., 3-EXO,3'-EXO-(1R,1'R)-BITHIOCAMPHOR - A VERSATILE SOURCE FOR FUNCTIONALLY DIFFERENT 3,3'-BIBORNANE DERIVATIVES .2. AN ACCESS TO 3-EXO,3'-EXO-(1R,1'R)-BICAMPHOR AND RELATED-COMPOUNDS, Tetrahedron, 51(48), 1995, pp. 13261-13270
Citations number
28
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
51
Issue
48
Year of publication
1995
Pages
13261 - 13270
Database
ISI
SICI code
0040-4020(1995)51:48<13261:3-AVSF>2.0.ZU;2-R
Abstract
3-exo,3'-exo-(1R,1'R)-bicamphor (12) is obtained from 3-exo,3'-exo-(1R ,1'R)-bithiocamphor (3) by condensation with hydrazine hydrate followe d by hydrolysis of the resulting dihydropyridazine 11. Deprotonation o f 12 with NaH and subsequent treatment with potassium hexacyanoferrate (III) furnishes the 2,2'-dioxo-3,3'-bibomanylidene 13, whilst reductio n of 12 with LiAlH4 affords the 3,3'-biisoborneol 16. Further related transformations to various 2,2'-difunctional 3,3'-bibomane derivatives are described, which are could be of interest as chiral ligands