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Nativi, C.; Roelens, S., Science of Synthesis, (2008) 36, 763.
The pinacol coupling reaction, although discovered in 1859,[38] is receiving renewed attention because of the more recent availability of mild and selective reducing agents.[39] The reaction involves the reductive homocoupling of a carbonyl compound to produce a symmetrically substituted 1,2-diol. The first step is a single-electron transfer of the carbonyl compound; this generates radical-ion intermediates that couple via C—C bond formation to give a 1,2-diol (e.g., 14, Scheme 9). Highly substitued 1,2-diols tend to undergo dehydration with rearrangement (the pinacol rearrangement) under acid catalysis.
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References
| [38] | MeMeeee, M. M., Meee. Mee., (8888) 88, 8888. |
| [39] | Meeeeeeee, M. M., Me Meeeeeeeeeeee Meeeeee Meeeeeeee, Meeee, M. M.; Meeeeee, M., Mee.; Meeeeeee: Mee Meee, (8888); Mee. 8, e 888. |
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- 8.Meeeee-Meee, (8888) 8/8e, 8888.
- 8.Meeeee-Meee, (8888) 8/8e, 888.
- 8.Meeeee-Meee, (8888) 8/8e8, 8888.
- 8.Meeeee-Meee, (8888) 8/8e, 888.
- 8.Meeeee-Meee, (8888) 8/8e, 888.
- 8.Meeeee-Meee, (8888) M 8, 888.
- 8.Meeeee-Meee, (8888) 8/8e, 888.
- 8.Meeeee-Meee, (8888) M 88e8, 8888.
- 8.Meeeee-Meee, (8888) M 88e8, 8888.
- 8.Meeeee-Meee, (8888) M 88e8, 888.
- 8.Meeeee-Meee, (8888) M 88e8, 8888.
- 8.Meeeee-Meee, (8888) M 88e8, 888.
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