Tetrahedron

Biquinones—III: The dimerisation of 1, 4-naphthaquinones

K Chandrasenan, RH Thomson

Index: Chandrasenan,K.; Thomson,R.H. Tetrahedron, 1971 , vol. 27, p. 2529 - 2539

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Citation Number: 19

Abstract

2-Methyl-1, 4-naphthaquinones, substituted at C-3 by alkyl, aralkyl, allyl, aryl or halogen groups, react in aqueous ethanolic NaOH to give dehydro-dimers, namely 1, 2-bis (1, 4- naphthaquinon-2-yl) ethanes. The reaction is analogous to the formation of bibenzyls from nitrotoluenes in basic media. In tBuOH containing tBuOK, 3-benzyl-2-methyl-1, 4- naphthaquinone also undergoes oxidation at the benzyl carbon atom to give phthiocol ...

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