Publication: Synthesis of 1-methyl-6,10-diphenylheptalene derivatives
Synthesis of 1-methyl-6,10-diphenylheptalene derivatives
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Jin, X., Linden, A., & Hansen, H. J. (2010). Synthesis of 1-methyl-6,10-diphenylheptalene derivatives. Helvetica Chimica Acta, 93(4), 729–745. https://doi.org/10.1002/hlca.200900435
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The reduction of heptalene diester 1 with diisobutylaluminium hydride (DIBAH) in THF gave a mixture of heptalene-1,2-dimethanol 2a and its double-bond-shift (DBS) isomer 2b (Scheme 3). Both products can be isolated by column chromatography on silica gel. The subsequent chlorination of 2a or 2b with PCl5 in CH2Cl2 led to a mixture of 1,2-bis(chloromethyl)heptalene 3a and its DBS isomer 3b. After a prolonged chromatographic separation, both products 3a and 3b were obtained in pure form. They crystallized smoothly from hexane/Et2O 7 : 1
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- Jin, X
- Hansen, H J
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Jin, X., Linden, A., & Hansen, H. J. (2010). Synthesis of 1-methyl-6,10-diphenylheptalene derivatives. Helvetica Chimica Acta, 93(4), 729–745. https://doi.org/10.1002/hlca.200900435
