Abstract
Incomplete catalytic hydrogenation of [2.2]metacyclophane (1) or 5,13-dimethyl[2.2]metacyclophane (2) yields (1,2,3,3arH, 4,5,9,10,10acH, 10btH)-decahydropyrene (9) and the dimethylanalogue10, resp.via atransanular cyclisation between positions 8 and 16. Under the same reaction conditions catalytic deuteration (D2, acetic acid-d1) affords a selectively deuterated10 (10-d5).9 is identical with as-decahydropyrene, obtained by high pressure hydrogenation of pyrene. The configurations of9 and10 were established by means of13C and1H-NMR spectroscopy and by comparison with10-d5.
A compound formerly believed to be as-decahydropyrene isomer is shown to be (±)-(1,2,3,3a,4,5,9,10)-octahydropyrene (4).
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Herrn Prof. Dr.F. Hecht zum 70. Geburtstag gewidmet.
Mit 4 Abbildungen
Auszugsweise vorgetragen bei der Tagung des Vereins Österreichischer Chemiker in Linz am 27. September 1973.
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Langer, E., Lehner, H. Stereoselektive Synthesen vons-Decahydropyrenen. Monatshefte für Chemie 104, 1484–1496 (1973). https://doi.org/10.1007/BF00909632
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DOI: https://doi.org/10.1007/BF00909632