Premium
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.
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom