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Dimopoulos P, George J, Tocher DA, et al. Mechanistic studies on the O-directed free-radical hydrostannation of disubstituted acetylenes with Ph3SnH and Et3B and on the iodination of allylically oxygenated alpha-triphenylstannylalkenes. Org Lett. 2005;7(24):5377-80doi: 10.1021/ol051937d.
Dimopoulos, P., George, J., Tocher, D. A., Manaviazar, S., & Hale, K. J. (2005). Mechanistic studies on the O-directed free-radical hydrostannation of disubstituted acetylenes with Ph3SnH and Et3B and on the iodination of allylically oxygenated alpha-triphenylstannylalkenes. Organic letters, 7(24), 5377-80. https://doi.org/10.1021/ol051937d
Dimopoulos, Paschalis, et al. "Mechanistic studies on the O-directed free-radical hydrostannation of disubstituted acetylenes with Ph3SnH and Et3B and on the iodination of allylically oxygenated alpha-triphenylstannylalkenes." Organic letters vol. 7,24 (2005): 5377-80. doi: https://doi.org/10.1021/ol051937d
Dimopoulos P, George J, Tocher DA, Manaviazar S, Hale KJ. Mechanistic studies on the O-directed free-radical hydrostannation of disubstituted acetylenes with Ph3SnH and Et3B and on the iodination of allylically oxygenated alpha-triphenylstannylalkenes. Org Lett. 2005 Nov 24;7(24):5377-80. doi: 10.1021/ol051937d. PMID: 16288510.
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Org Lett. 2005 Nov 24;7(24):5377-80. doi: 10.1021/ol051937d.

Mechanistic studies on the O-directed free-radical hydrostannation of disubstituted acetylenes with Ph3SnH and Et3B and on the iodination of allylically oxygenated alpha-triphenylstannylalkenes.

Organic letters

Paschalis Dimopoulos, Jonathan George, Derek A Tocher, Soraya Manaviazar, Karl J Hale

Affiliations

  1. The Christopher Ingold Laboratories, The Chemistry Department, University College London, 20 Gordon Street, London WC1H 0AJ, United Kingdom.

PMID: 16288510 DOI: 10.1021/ol051937d

Abstract

[reaction: see text] The free-radical hydrostannation of 1 with Ph(3)SnH and catalytic Et(3)B in PhMe has been mechanistically probed. At high Ph(3)SnH concentrations, the O-directed hydrostannation pathway dominates, and 2 is formed with good selectivity (ca. 11.1:1). Substantially lower stannane/substrate concentrations increase the amount of tandem 5-exo-trig cyclization product 3 that is observed.

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