The [1,5]-Brook rearrangement: an initial application in anion relay chemistry.
The [1,5]-Brook rearrangement proceeds efficiently in a series of hydroxyl dithiane substrates with sodium and potassium bases; less effective are lithium bases. That the mode of silyl migration is intramolecular was demonstrated by a crossover experiment. Finally, the tricomponent anion relay chemistry (ARC) coupling tactic was demonstrated employing the [1,5]-Brook rearrangement.
Smith
Amos B
AB
Department of Chemistry, Laboratory for Research on the Structure of Matter, and Monell Chemical Senses Center, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA. smithab@sas.upenn.edu
Xian
Ming
M
Kim
Won-Suk
WS
Kim
Dae-Shik
DS
D000838:Anions / Q000737:chemistry; D012821:Silanes / Q000737:chemistry*; D013440:Sulfides / Q000737:chemistry*; D014297:Trimethylsilyl Compounds / Q000737:chemistry
D000838:Anions; D012821:Silanes; D013440:Sulfides; D014297:Trimethylsilyl Compounds