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Heterotricyclodecane. XXVI . 2,6‐Dioxatricyclo [3.3.2.0 3,7 ]decan, ein neuartiges isomers von 2,6‐dioxaadamantan
Author(s) -
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.19800630426
Subject(s) - chemistry , decane , heteroatom , cyclooctane , stereochemistry , ring (chemistry) , organic chemistry , cyclohexane
2,6‐Dioxatricyclo [3.3.2.0 3,7 ]decane, a Novel Isomer of 2,6‐Dioxaadamantane Restriction among the great number of possible diheterotricyclodecanes to such with a carbocyclic 8membered ring (cyclooctane) as basic skeleton, which is crosswise bridged by two heteroatoms, and restriction to 5‐, 6‐ and 7membered heterocyclic rings results in the isomeric diheterotricyclodecanes of the following five different structural types: 2,6‐diheteroadamantane (a) , 2,7‐diheteroisotwistane (b) , 2,7‐diheterotwistance (c) , 2,8‐diheterohomotwistbrendane (d) , and 2,6‐diheterotricyclo [3.3.2.0 3,7 ]decane (e ; s. Scheme 1 ). Starting from a suitably C (5) o(2) ‐functionalized 2,7‐dioxaisotwistane, first representatives with the hitherto unknown skeleton of type e were prepared by molecular rearrangement involving neighboring group participation: 2,6‐dioxatricyclo [3.3.2.0 3,7 ]decane (41) and the derivatives 34–40 thereof (Scheme 7) .