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Tricyclo [3.3.2.0 3,7 ]decan (9‐Homo‐nor‐adamantan) Synthese und Umwandlungen
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.19800630735
Subject(s) - chemistry , decane , adamantane , thionyl chloride , solvolysis , phosphorus pentachloride , medicinal chemistry , propellane , stereochemistry , chloride , organic chemistry , bicyclic molecule , hydrolysis
Tricyclo[3.3.2.0 3,7 ]decane (9‐Homo‐nor‐adamantane). Synthesis and Transformations A synthesis of tricyclo [3.3.2.0 3,7 ]decane (=9‐homo‐nor‐adamantane; 1 ), which belongs to the adamantaneland, a family of nineteen isomeric C 10 H 16 hydrocarbons, is described, as well as derivatives thereof. Treatment of protoadamantan‐5 endo ‐ol (11) with either thionyl chloride or phosphorus pentachloride yielded under rearrangement the chloride 18 , and solvolysis of the 5 endo ‐chloro‐protoadamantane (16) led to the acetate 26, 18 and 26 having both the tricyclo [3.3.2.0 3,7 ]decane skeleton. Subsequent transformations gave the title compound 1 as well as the corresponding olefin 8 .
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