Adelaide Research & Scholarship
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https://hdl.handle.net/2440/68635
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| Type: | Journal article |
| Title: | 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 |
| Author: | Dimopoulos, P. George, J. Tocher, D. Manaviazar, S. Hale, K. |
| Citation: | Organic Letters, 2005; 7(24):5377-5380 |
| Publisher: | Amer Chemical Soc |
| Issue Date: | 2005 |
| ISSN: | 1523-7060 1523-7052 |
| Statement of Responsibility: | Paschalis Dimopoulos, Jonathan George, Derek A. Tocher, Soraya Manaviazar, and Karl J. Hale |
| 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. |
| Rights: | Copyright © 2005 American Chemical Society |
| DOI: | 10.1021/ol051937d |
| Published version: | http://dx.doi.org/10.1021/ol051937d |
| Appears in Collections: | Aurora harvest Chemistry publications |
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