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Facile route to 1-phosphoryl- and 1-sulfonyl-1,3-dienes via palladium-catalyzed elimination of allylic acetates

✍ Scribed by Björn Åkermark; Jan-E. Nyström; Tobias Rein; Jan-E. Bäckvall; Paul Helquist; Robert Aslanian

Publisher
Elsevier Science
Year
1984
Tongue
French
Weight
271 KB
Volume
25
Category
Article
ISSN
0040-4039

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✦ Synopsis

The palladium(II)-catalyzed chloroacetoxylation of 1,3-dienes is employed to prepare 1-chloro-4-acetoxy-2-alkenes which are then transformed into 1-phosphoryl-or lsulfonyl-4-acetoxy-2-alkenes respectively. Elimination of acetate is promoted by palladium(O)-catalysis or by sodium hydride, producing the useful 1-phosphoryl-or lsulfonyl-1,3-dienes.

Table Condi-Condi-Chloroacetate tionsa Intermediate,yieldb(E/Z) tionsa Diene products, yieldbWZ)

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