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9,10‐Dimetallatriptycenes of Group 14: A Novel Synthetic Approach from ortho ‐Phenylenemagnesium
Author(s) -
Dam Matheus A.,
Akkerman Otto S.,
De Kanter Franciscus J. J.,
Bickelhaupt Friedrich,
Veldman Nora,
Spek Anthony L.
Publication year - 1996
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.19960020916
Subject(s) - group (periodic table) , reagent , chemistry , crystal structure , medicinal chemistry , stereochemistry , crystallography , organic chemistry
9,10‐Dimetallatriptycenes of Group 14 are readily accessable by a novel synthetic approach: reaction of ortho ‐phenylenemagnesium ( 1 ) with RMCl 3 afforded 9,10‐dimethyl‐9,10‐dimetallatriptycenes ( 3 ; M = Si, Ge, Sn) or 9, 10‐dimethyl‐9‐germa‐10‐stannatriptycene ( 11 ). The reaction can even be tuned to afford unsymmetrically substituted triptycenes such as 9‐methyl‐10‐phenyl‐9,10‐digermatriptycene ( 8 ); in some of these reactions, strong indications were obtained for the intermediacy of tri‐Grignard reagents RM(2‐C 6 H 4 MgCl) 3 ( 5, 10 ). The new triptycenes were characterised by their spectral data and in the case of 3c (M = Sn) by an X‐ray crystal structure determination.