Synthesis of spiro-compounds: use of diselenoacetals for generation of quaternary centres by alkylation and radical cyclization

L Set, DR Cheshire, DLJ Clive

Index: Set, Lu; Cheshire, David R.; Clive, Derrick L. J. Journal of the Chemical Society, Chemical Communications, 1985 , # 17 p. 1205 - 1207

Full Text: HTML

Citation Number: 13

Abstract

Ketones are readily converted viathe corresponding diphenyl diselenoacetals (2) into selenides (5) which undergo radical 5-exo cyclization to spiro-compounds (7) on treatment with triphenyltin hydride and azoisobutyronitrile; an analogous sequence serves for the preparation of spiro-lactones (12).

Related Articles:

N, N-diethylbenzeneselenamide: a useful reagent for the direct selenenylation of aldehydes

[Jefson, Martin; Meinwald, Jerrold Tetrahedron Letters, 1981 , vol. 22, # 37 p. 3561 - 3564]

α-Phenylselenenylation d'aldehydes-synthese simple d'α-cetoaldehydes a fonction cetone protegee

[Paulmier, Claude; Lerouge, Patrice Tetrahedron Letters, 1982 , vol. 23, # 15 p. 1557 - 1560]

A mild oxidation of aldehydes to α, β-unsaturated aldehydes

[Williams, David R.; Nishitani, Kiyoshi Tetrahedron Letters, 1980 , vol. 21, p. 4417 - 4420]

A mild oxidation of aldehydes to α, β-unsaturated aldehydes

[Williams, David R.; Nishitani, Kiyoshi Tetrahedron Letters, 1980 , vol. 21, p. 4417 - 4420]

More Articles...