Methoxybenzo [a] pyrene 4, 5-oxides labeled with carbon-13: electronic effects in the NIH shift

IR Silverman, GH Daub…

Index: Silverman, I. Robert; Daub, Guido H.; Jagt, David L. Vander Journal of Organic Chemistry, 1985 , vol. 50, # 26 p. 5550 - 5556

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Citation Number: 6

Abstract

The syntheses of 3a and 3b are outlined in Scheme I. Our strategy for incorporating the labeled carbons toward the end of the reaction scheme required initial construction of a chrysene skeleton. Starting with the appropriate methoxytetralone, treatment with ethyl lithioactate5 followed by dehydration and dehydrogenation (Pd/C, 250" C) provided ester 7 in 17% yield. Conversion of 7 to bromide 10 was achieved in 16% yield over three steps: ...