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2004
Organo-selenium compounds
S 0130
Synthesis of Substituted Se-Phenyl Selenocarboxylates from Terminal Alkynes.
Reaction of phenylselenoalkynes (I) and (IX), obtained by selenylation of terminal
49- 160 —
alkynes, with toluenesulfonic acid monohydrate provides an efficient access towards
Se-phenyl selenocarboxylates (II) and (X), respectively. A wide range of functional
groups is tolerated, including ester, ether, carbonyl, sulfonamide, amide, phthalimide
groups and C—C double bonds. The phenylselenyl group can be substituted readily
with amines or alcohols to afford the corresponding functionalized amides (IV), (XII)
or esters (XIV). It is shown, however, that phenylselenoalkynes (XVII) containing a
propargylic oxy group undergo a different elimination pathway to afford α,β-unsaturated selenocarboxylates (XVIII). — (TIECCO*, M.; TESTAFERRI, L.; TEMPERINI,
A.; BAGNOLI, L.; MARINI, F.; SANTI, C.; TERLIZZI, R.; Eur. J. Org. Chem. 2004,
16, 3447-3458; Dip. Chim. Tecnol. Farm., Univ. Perugia, I-06123 Perugia, Italy;
Eng.) — Mischke
2004
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