135650-63-4Relevant academic research and scientific papers
A Novel Competition between C-Se and C-Si Cleavage in Cyclization of β-Seleno-β-silyl-substituted Divinyl Ketones
Yamazaki, Shoko,Mizuno, Wataru,Yamabe, Shinichi
, p. 1555 - 1560 (2007/10/02)
Reactions of β-seleno-β-silyl-substituted divinyl ketones 2-4 with Lewis acid at room temp. gave phenylseleno and/or trimethylsilyl functionalized cyclopentanones.The use of TiCl4 or SnCl4 results in C-Se cleavage leading to 5-(phenylseleno)-3-(trimethylsilyl)cyclopent-2-enones 9-11 as major products.In contrast, using AgBF4-TMSCl (trimethylsilyl chloride) results in C-Si cleavage to give 3-(phenylseleno)cyclopenten-2-ones 12-14.Lewis acid-dependent competitive cleavage between C-Se and C-Si bonds has been demonstrated.
