Mechanistic Studies on the Samarium Diiodide -Promoted Cyclization of N-Iodoalkyl Cyclic Imides

Bulletin of the Korean Chemical Society

Volumn 18, Issue 10, 1997, Pages 1039-1041

  Ha, Deok Chan ^a   Yun, Chang Soo ^a  

^a Korea University   (South Korea)

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[No Author keywords available]

Indexed keywords

EID: 0031317504     PISSN: 02532964     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (22)

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19. To compare the relative reduction potentials of the imide carbonyls, 1 and 2 were reacted with Zn/AcOH in ether at room temperature. Phthalimide 2a was reduce to give 6c, and partially reduced 6b was obtained from 2b. Under the same condition, succinimide and gluterimide derivatives 1 provided dehalogenated products and carbonyl reduction was not observed.
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21. Reactions of 1 and 2a with tri-n-butyltin hydride and AIBN under high dilution condition produced deiodinated reduction products in quantitative yields. Thus, the possibility of radical cyclization was disregarded. For radical cyclization and ring expansion reaction of 2-haloalkyl-1,3-dicarbonyl systems, see: (a) Dowd, P.; Choi, S. C. J. Am. Chem. Soc. 1987, 109, 6548.
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