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Phenylation of the 5,11‐diazaditwistane nucleus
Author(s) -
Kozlowski Matthew A.,
Broeke Jan Ten,
Grabowski Eklward J. J.
Publication year - 1979
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570160344
Subject(s) - chemistry , aluminum hydride , dodecane , decarboxylation , benzene , hydrolysis , medicinal chemistry , organic chemistry , ion , catalysis , methoxide
A simple phenylation of the 5,11‐diazatetracyclo[6.2.2.0 2,7 0 4,9 ]dodecane system (5,11‐diazaditwistane) is described. Phenylative decarboxylation of 5,11‐biscarbethoxy‐5,11‐diazatetracyclo[6.2.2.0 2,7 .0 4,9 ]dodecane‐2,9‐dicarboxylic acid ( 3 ) with lead tetraacetate in benzene affords the 2,9‐diphenyl analogue ( 4 ). Hydrolysis yields 2,9‐diphenyl‐5,11‐diazatetracyclo‐[6.2.2.0 2,7 .0 4,9 ]dodecane ( 5 ), whereas lithium aluminum hydride affords the 5,11‐dimethyl analogue ( 6 ).