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1,2 endo ‐Trimethylenenorbornane. A novel isomer of adamantane
Author(s) -
Jäggi Franz Josef,
Ganter Camille
Publication year - 1980
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19800630414
Subject(s) - chemistry , adamantane , regioselectivity , diimide , intramolecular force , stereoselectivity , cycloaddition , double bond , stereochemistry , bromide , medicinal chemistry , organic chemistry , molecule , catalysis , perylene
Abstract An easy approach to the novel adamantane isomer 1,2 endo ‐trimethylenenorbornane (2) is described. Starting from a mixture of pent‐4‐ynylcyclopentadienes 3 the tricyclic monosaturated key intermediate 5 was prepared by intramolecular cycloaddition (→ 4 ) and subsequent regioselective reduction of the C(5), C(6) double bond. The title hydrocarbon 2 was obtained from 5 upon stereoselective hydrogenation by diimide. In addition specifically deuteriated analogues of 2 were prepared applying dideuteriodiimide. Compound 2 rearranged to 2 endo , 6 endo ‐trimethylenenorbornane (4‐homobrendane, 10 ) in sulfuric acid as well as with aluminium bromide in carbon disulfide.