Stereoselektive Synthesen vons-Decahydropyrenen

摘要

Incomplete catalytic hydrogenation of 2.2metacyclophane (1) or 5,13-dimethyl2.2metacyclophane (2) yields (1,2,3,3arH, 4,5,9,10,10acH, 10btH)-decahydropyrene (9) and the dimethylanalogue10, resp.viaatransanular cyclisation between positions 8 and 16. Under the same reaction conditions catalytic deuteration (D2, acetic acid-d1) affords a selectively deuterated10(10-d5).9is identical with as-decahydropyrene, obtained by high pressure hydrogenation of pyrene. The configurations of9and10were established by means of13C and1H-NMR spectroscopy and by comparison with10-d5.