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3SnH cyclization is not usually observed: J. D. Kilburn. Tetrahedron Lett. 31, 2193 (1990); P. M. Esch, H. Heimstra and W. N. Speckamp. Tetrahedron Lett. 31, 759 (1990); S. Knapp, F. S. Gibson and Y. H. Choe. Tetrahedron Lett. 31, 5397 (1990). However in favorable cases cyclization can be observed: R. Tsang and B. Fraser-Reid. J. Am. Chem. Soc. 108, 2116 (1986). Sometimes 5-exo cyclization is not observed even under high dilution.
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3SnH cyclization is not usually observed: J. D. Kilburn. Tetrahedron Lett. 31, 2193 (1990); P. M. Esch, H. Heimstra and W. N. Speckamp. Tetrahedron Lett. 31, 759 (1990); S. Knapp, F. S. Gibson and Y. H. Choe. Tetrahedron Lett. 31, 5397 (1990). However in favorable cases cyclization can be observed: R. Tsang and B. Fraser-Reid. J. Am. Chem. Soc. 108, 2116 (1986). Sometimes 5-exo cyclization is not observed even under high dilution.
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Esch, P.M.1
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6
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3SnH cyclization is not usually observed: J. D. Kilburn. Tetrahedron Lett. 31, 2193 (1990); P. M. Esch, H. Heimstra and W. N. Speckamp. Tetrahedron Lett. 31, 759 (1990); S. Knapp, F. S. Gibson and Y. H. Choe. Tetrahedron Lett. 31, 5397 (1990). However in favorable cases cyclization can be observed: R. Tsang and B. Fraser-Reid. J. Am. Chem. Soc. 108, 2116 (1986). Sometimes 5-exo cyclization is not observed even under high dilution.
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Knapp, S.1
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Sometimes 5-exo cyclization is not observed even under high dilution
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3SnH cyclization is not usually observed: J. D. Kilburn. Tetrahedron Lett. 31, 2193 (1990); P. M. Esch, H. Heimstra and W. N. Speckamp. Tetrahedron Lett. 31, 759 (1990); S. Knapp, F. S. Gibson and Y. H. Choe. Tetrahedron Lett. 31, 5397 (1990). However in favorable cases cyclization can be observed: R. Tsang and B. Fraser-Reid. J. Am. Chem. Soc. 108, 2116 (1986). Sometimes 5-exo cyclization is not observed even under high dilution.
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A. L. J. Beckwith, C. J. Easton, T. Lawrence and A. K. Serelis. Aust. J. Chem. 36, 545 (1983). gem-Dimethyl substitution in a 5-hexenyl radical at C-2, C-3 and C-4 increases the rate of cyclization at 25°C by 15-, 22- and 14-fold, respectively.
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2 undergoes 5-exo cyclization ca 40 times faster than the 5-hexenyl radical itself at 25°C: A. L. J. Beckwith and C. H. Schiesser. Tetrahedron 41, 3925 (1985).
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3SiH with the corresponding bromides gives good yields of the cyclized amines, indicating preferential radical attack at the halogen: S. Kim, G. H. Joe and J. Y. Do. J. Am. Chem. Soc. 116, 5521 (1994).
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