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Synthesen von Tricyclo [5.2.1.0 4,8 ]decan (2‐Homobrendan)
Author(s) -
Jäggi Franz Josef,
Buchs Peter,
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.19800630415
Subject(s) - chemistry , decane , bicyclic molecule , medicinal chemistry , ene reaction , stereochemistry , organic chemistry
Syntheses of Tricyclo [5.2.1.0 4,8 ]decane (2‐Homobrendane) Three different approaches to tricyclo [5.2.1.0 4,8 ] decane (5) (and derivatives thereof), one of the 19 isomeric hydrocarbons of the ‘adamantaneland’, are described: (1) Cyclization of properly functionalized bicyclo [3.2.1]octanes as 32 (cyclialkylation), 40+42 (thermocyclization) and 44+45 (photocyclization); (2) Silver‐(I)‐ion catalyzed rearrangement of 5,7‐ and 5,10‐Dehydroprotoadamantane ( 63 and 64 , respectively) yielding tricyclo[5.2.1.0 4,8 ]dec‐2‐ (39) and ‐5‐ene (59) , respectively; (3) Thermal eliminative rearrangement of the 10 endo‐p ‐toluenesulfonate and ‐methanesulfonate of protoadamantane ( 71 and 72 ) and protoadamant‐4‐ene ( 76 and 77 ), respectively, yielding tricyclo [5.2.1.0 4,8 ]dec‐2‐ene (39) and ‐2, 5‐diene (15) , respectively.