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Synthesis and Acid Catalyzed Rearrangement of Cage Propellanes
Author(s) -
Kotha Sambasivarao,
Cheekatla Subba Rao
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201903441
Subject(s) - synthon , propellane , chemistry , cycloaddition , ring (chemistry) , stereochemistry , ring closing metathesis , nonane , lewis acids and bases , derivative (finance) , cage , catalysis , metathesis , combinatorial chemistry , bicyclic molecule , organic chemistry , polymer , mathematics , combinatorics , financial economics , economics , polymerization
The design and synthesis of highly decorated cage [4.3.2]propellanes and D 3 ‐trishomocubanes have been reported via ring‐closing metathesis (RCM), [4+2] cycloaddition and acid‐catalyzed rearrangement as key steps. These cage polycycles were prepared starting with inexpensive synthons such as 2,5‐dimethoxybenzaldehyde and endo‐dicyclopentadiene. Propellanes containing fused spiro[4.4]nonane ring system was realized by RCM protocol. Interestingly, the dimethoxy cage propellane derivative was observed instead of the rearranged product with Lewis acid such as BF 3 ⋅ MeOH. Several intricate cage structures were synthesized from rearrangement approach that are difficult to generate by conventional routes.