Tetrahedron

Efficient syntheses of some 1-naphthylalkyl ketones and studies on their autooxidation in basic medium

A Chatterjee, SR Raychaudhuri, SK Chatterjee

Index: Chatterjee, A.; Raychaudhuri, S. R.; Chatterjee, S. K. Tetrahedron, 1981 , vol. 37, # 21 p. 3653 - 3660

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Citation Number: 6

Abstract

Birch reductions of 4, 6-dimethoxy-1-naphthylalkyl ketones 1 provided in fair to good yields the demethoxylated products, 6-methoxy-1-naphthylalkyl ketones 2 (a–g), not easily accessible by other procedures. Autooxidation of these ketones in basic medium afforded the diketones 6 (a–c), the acid 2h, and interestingly the phenol 5. Extension of this reduction to the related tricyclic ketone 8 afforded 9a, the phenolic ketone 9b; and significantly the ...