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Stereoselective synthesis and reactions of 1-seleno-4-tert-butyl cyclohexyllithiums

✍ Scribed by A. Krief; G. Evrard; E. Badaoui; V. De Beys; R. Dieden

Publisher: Elsevier Science
Year: 1989
Tongue: French
Weight: 293 KB
Volume: 30
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)93818-3

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✦ Synopsis

The axial C-Se bond of seleno-and mixed selenoacetak derivedfrom I-tert-butyl cyc2ohexanones exhibit a high tendency to be cleaved by n-butyllithium. The resulting 1 -selerw+tert-butyl cyclohexyllithium are selective& protonated or seIenyIated via axial attack.

We recently described 1 that l,l-bis@henylseleno)4tert-butyl cyclohexane b reacts with n-butyllithium to provide, after hydrolysis, I-(phenylseleno)-4-tert-butyl cyclohexane 4 (trans/cis : 96 / 4) with almost

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