Abstract
Catalytic hydrogenation of [2.2]metacyclophane yieldscis-cis-anti-cis-cis-hexadecahydropyrene (4) by a transanular cyclization between positions 8 and 16.4 can be isomerized to givetrans-trans-anti-trans-trans-hexadecahydropyrene (1), so far the only known configurational isomer of that tetracyclane series. The configuration of4 was established by means of13C-N M R- and1H-N M R-spectroscopy as well as by1H-N M R-studies of selectively deuterated4 (4-d10), accessible by catalytic deuteration of [2.2]metacyclophane.
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Herrn Prof. Dr.F. Hecht zum 70. Geburtstag gewidmet.
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Langer, E., Lehner, H. Stereochemie der Polycyclane, 1. Mitt.: Synthese voncis—cis—anti—cis—cis-Hexadecahydropyren durch stereoselektive hydrierung des [2.2]Metacyclophans. Monatshefte für Chemie 104, 1154–1163 (1973). https://doi.org/10.1007/BF00910030
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DOI: https://doi.org/10.1007/BF00910030