Synthesis

Synthesis of new 3-(-2-alkenyl)-2-hydroxy-5-methoxy-p-benzoquinones via Claisen rearrangement of original 5-methoxy-4-(2-propenyloxy)-o-benzoquinones

O Reinaud, P Capdevielle, M Maumy

Index: Reinaud, Olivia; Capdevielle, Patrice; Maumy, Michel Synthesis, 1988 , # 4 p. 293 - 300

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Citation Number: 6

Abstract

The Claiscn rearrangement is extended to compounds containing the benzoquinone moiety, obtained by regioselective nucleophilic substi-tution on 4-(p-methoxyphenoxy)-5-methoxy-o- benzoquinone (I). In the most general case, 5-methoxy-4-(2-propenyloxy)-0-benzoquinones 3 rearrange quantitatively into (E)-3-(2-alkenyl-2-hydroxy-5~ methoxy-p-benzoquinones 4. Furfuryl or (2-thienyl) metl1yl ethers isomerizc lo 3-(2-rnethyl-3-furyl)-and 3-(2-rnethyl-3- ...