Lewis acid-induced rearrangment of α-[bis(methylthio)methylene]-ethyl-2-styrylcyclopropylcarbinols: Unexpected formation of a novel bicyclo[3.2.1]octadiene framework

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue 10, 2000, Pages 1547-1550

  Syam Kumar, U K ^a   Patra, Pranab K ^a   Ha, Hiriyakkanavar ^a   Junjappa, Hiriyakkanavar ^a   Bharadwaj, Parimal K ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; DERIVATIVES; INORGANIC ACIDS; KETONES; MOLECULAR STRUCTURE; X RAY DIFFRACTION ANALYSIS;

LEWIS ACIDS;

AROMATIC COMPOUNDS;

EID: 0034697430     PISSN: 14704358     EISSN: None     Source Type: Journal    
DOI: 10.1039/b001043j     Document Type: Article

References (13)

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3. B. Patro, B. Deb, H. Ila and H. Junjappa, J. Org. Chem., 1992, 57, 2257.
4. B. Patro, B. Deb, H. Ila and H. Junjappa, Tetrahedron, 1994, 50, 255.
5. P. K. Patra, B. Patro, H. Ila and H. Junjappa, Tetrahedron Lett., 1993, 34, 3951.
6. P. K. Patra, V. Sriram, H. Ila and H. Junjappa, Tetrahedron, 1998, 54, 531.
7. The X-ray crystallographic structure for 10a was unfortunately not of sufficient quality to publish, but did confirm the general connectivity. We are attempting a low-temperature study which will be reported elsewhere.
8. Such kinds of steric effects have been observed in cationic rearrangement of substituted cyclopropyl carbinols: T. S. Sorensen and K. Rajeswari, J. Am Chem. Soc., 1971, 93, 4222;
9. K. Rajeswari and T. S. Sorensen, J. Am. Chem. Soc., 1973, 95, 1239;
10. N. W. K. Cheu and T. S. Sorensen, Can. J. Chem., 1973, 51, 2776;
11. R. Bladek and T. S. Sorensen, Can. J. Chem., 1972, 50, 2806.
12. Our attempts to obtain bicyclo[3.3.0]octadiene derivatives 8 or 19 from the respective carbinols 5 or 9 under varying conditions using different Lewis/protic acids were not successful.
13. P. Ghosh and P. K. Bharadwaj, J. Chem. Soc., Dalton Trans., 1997, 2673.