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Palladium‐Catalyzed Allylic Substitution of Allyl Vinyl Carbonate
Author(s) -
Mori Miwako,
Nishimata Toyoki,
Nagasawa Yuji,
Sato Yoshihiro
Publication year - 2001
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/1615-4169(20010129)343:1<34::aid-adsc34>3.0.co;2-9
Subject(s) - chemistry , allylic rearrangement , palladium , carbonate , nucleophile , catalysis , organic chemistry , dimethyl carbonate , medicinal chemistry , polymer chemistry
Vinyl carbonate was found to be a very effective leaving group in palladium‐catalyzed allylic substitution. When the reaction of an equimolar amount of allyl methyl carbonate and allyl vinyl carbonate with dimethyl malonate was carried out in the presence of a palladium catalyst, allyl vinyl carbonate reacted with the nucleophile, and most of allyl methyl carbonate remained unchanged. In the reaction of a compound having allyl methyl carbonate and allyl vinyl carbonate in the molecule with tosyl amide, in the presence of a palladium catalyst, the nucleophile reacted with the allyl vinyl carbonate, and the allyl methyl carbonate remained unchanged.