ISSN:
1434-4475
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
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).
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF00909632
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