4.8 Article

Dual pathways for the desilylation of silylamines by singlet oxygen

Journal

ORGANIC LETTERS
Volume 8, Issue 9, Pages 1783-1786

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol0602607

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A kinetic and product study has been carried out for the reactions of silylamines 1a and 1b with O-1(2) in MeCN and (80:20) MeCN-MeOH. Indications suggesting an electron-transfer step following exciplex (1) formation have been obtained. However, the fate of the radical cation is solvent dependent. The radical cation undergoes desilylation in MeCN-MeOH and deprotonation in MeCN.

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