A new synthetic method for cyclic allenes and acetylenes. Cleavage of a C-C bond directed by a silyl group

Synlett

Volumn , Issue SPEC. ISS., 1997, Pages 461-462

  Sugai, Masaharu ^a   Tanino, Keiji ^a   Kuwajima, Isao ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0009512293     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-6150     Document Type: Article

References (11)

1. Hesse, M. Ring Enlargement in Organic Chemistry; VCH: Weinheim, 1991.
2. Ho, T.-L. Heterolytic Fragmentation of Organic Molecules; J. Wiley & Sons: New York, 1993.
3. We have already reported that a δ-silyl cationic species undergoes rearrangement reactions rather than a fragmentation reaction: Tanino, K.; Hatanaka, Y.; Kuwajima, I. Chem. Lett., 1987, 385.
4. Stang, P. J.; Rappoport, Z.; Hanack, M.; Subramanian, L. R. Vinyl Cations; Academic Press: New York, 1979.
5. The stereochemistry of ketol 4 was assigned as follows: The cis configuration of the angular methyne proton and the silylmethyl group was determined by observation of NOE. The stereochemistry of the hydroxy group was assigned by the coupling constant (J = 11 Hz) between the angular methyne proton and the α-proton of the hydroxy group.
6. Dueber, T. E.; Stang, P. J.; Pfeifer, W. D.; Summerville, R. H.; Imhoff, M. A.; Schleyer, P. v. R.; Hummel, K.; Bocher, S.; Harding, C. E.; Hanack, M. Angew. Chem., 1970, 82, 517.
7. Johnson, R. P. Chem. Rev. 1989, 89, 1111 and references cited therein.
8. PM3 calculations on 6-methylene-1,2-cyclodecadiene and 7-methylene-2-vinylcyclooctene were performed, and the results indicate that the latter is 11.1 kcal/mol more stable than the former.
9. (a) Pfeifer, W. D.; Bahn, C. A.; Schleyer, P. v. R.; Bocher, S.; Harding, C. E.; Hummel, K.; Hanack, M.; Stang, P. J. J. Am. Chem. Soc., 1971, 93, 1513.
10. (b) Hanack, M.; Bentz, H.; Märkel, R.; Subramanian, L. R. Justus Liebigs Ann. Chem. 1978, 1894.
11. (c) McNeely, S. A.; Kropp, P. J. J. Am. Chem. Soc. 1976, 98, 4319.