A Novel Synthesis of 2-Methyl-3 : 4-Benzphenanthrene

Abstract

IT has been observed that 2-methyl-3 : 4-benzphenanthrene1,2 is a potent carcinogenic hydrocarbon3. Although this hydrocarbon was synthesized previously by Hewett1 and by Newman2, their methods are rather laborious and involve numerous steps, and eventually make this hydrocarbon less accessible to synthetic chemists. However, the method developed in this laboratory for synthesis of polycyclics4,5 was extended to the synthesis of the above hydrocarbon. The synthesis of 9-methyl-phenanthrene6 served as a model for this synthesis, which gave 2-methyl-3 : 4-benzphenanthrene in excellent over-all yield in four steps starting from 2-allyl-l-tetralone.

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References

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    Hewett, J. Chem. Soc., 596 (1936).

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    Newman and Joshel, J. Amer. Chem. Soc., 62, 972 (1940).

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    Bachmann, Cook, Dansi, de Worms, Haslewood, Hewett and Robinson, Proc. Roy. Soc., B, 123, 359 (1937).

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    Bhattacharyya and Mukherji, Science and Culture, 16, No. 8, 374 (1951).

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    Cologne and Pichat, Bull. Soc. Chim., France, 853 (1949).

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    Bhattacharyya and Mukherji, Experientia (in the press).

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    Birch and Mukherji, J. Chem. Soc., 2536 (1949).

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    Cf. Kloetzel, J. Amer. Chem. Soc., 62, 1171 (1940).

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    Cf. Bogert and Davidson, J. Amer. Chem. Soc., 56, 961 (1934).

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MUKHERJI, S., RAO, P. A Novel Synthesis of 2-Methyl-3 : 4-Benzphenanthrene. Nature 168, 1041 (1951). https://doi.org/10.1038/1681041a0

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