Stereoselective Cyclizations and Rearrangements in Vinyl Radicals Promoted by Regioselective Sulfanyl Radical Addition to Enynes

Journal of Organic Chemistry

Volumn 62, Issue 16, 1997, Pages 5600-5607

  Montevecchi, Pier Carlo ^a   Navacchia, Maria Luisa ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000241582     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9701142     Document Type: Article

References (61)

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40. It is well known that radical species, including arenesulfanyl (Broka, C. A.; Reichert, D. E. C. Tetrahedron Lett. 1987, 28, 1503), selenyl (ref 7d), and stannyl radicals (ref 16a) promote the cyclization of enynes by regioselective addition to the CC triple bond. These radicals facilely add to both CC double and triple bonds of enynes leading to alkyl and vinyl radical intermediates. The reason for the regioselective addition is the greater reversibility of radical addition to alkenes compared with alkynes (see ref 1a).
41. Preliminary results have been previously reported; see: Montevecchi, P. C.; Navacchia, M. L. Tetrahedron Lett. 1996, 37, 6583.
42. Compound (Z)-23 was contaminated by minor amounts of its (E)-isomer [Z/E ratio ca. 9:11 probably deriving from a postisomeriza- tion process.
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51. 1,4-Hydrogen migrations are very rare. For examples see: Brunton, G.; Griller, D.; Barclay, L. R. C.; Ingold, K. U. J. Am. Chem. Soc. 1976, 98, 6803. Journet, M.; Malacria, M. J. Org. Chem. 1992, 57, 3085. Wallace, T. J.; Gritter, R. J. J. Org. Chem., 1961, 26, 5256.
52. 1,4-Hydrogen migrations are very rare. For examples see: Brunton, G.; Griller, D.; Barclay, L. R. C.; Ingold, K. U. J. Am. Chem. Soc. 1976, 98, 6803. Journet, M.; Malacria, M. J. Org. Chem. 1992, 57, 3085. Wallace, T. J.; Gritter, R. J. J. Org. Chem., 1961, 26, 5256.
53. 1,4-Hydrogen migrations are very rare. For examples see: Brunton, G.; Griller, D.; Barclay, L. R. C.; Ingold, K. U. J. Am. Chem. Soc. 1976, 98, 6803. Journet, M.; Malacria, M. J. Org. Chem. 1992, 57, 3085. Wallace, T. J.; Gritter, R. J. J. Org. Chem., 1961, 26, 5256.
54. The (E) configuration of the 6-(π-exo)exo cyclization product 42 and the 5-(π-exo)exo product 25 was attributed on the basis of the general evidence provided by related cyclization products 17, 24, and 43, whose (E) configurations were assigned by NOE measurements.
55. In particular, the absolute rate of addition of butanesulfanyl radicals to cyciopropylethytene and 1-octene (McPhee, D. J.; Campredon, M.; Lesage, M.; Griller, D J. Am. Chem. Soc. 1989, 111, 7563) and 1-pentene ( Sivertz, C. J. Phys. Chem. 1959, 63, 34) have been reported.
56. In particular, the absolute rate of addition of butanesulfanyl radicals to cyciopropylethytene and 1-octene (McPhee, D. J.; Campredon, M.; Lesage, M.; Griller, D J. Am. Chem. Soc. 1989, 111, 7563) and 1-pentene ( Sivertz, C. J. Phys. Chem. 1959, 63, 34) have been reported.
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