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New Monomers for Organometallic Poly‐ p ‐xylylenes: Synthesis of Silyl‐, Germyl‐ and Stannyl[2.2]paracyclophane Derivatives
Author(s) -
Popova Elena,
Antonov Dmitrii,
Sergeeva Elena,
Vorontsov Evgenii,
Stash Adam,
Rozenberg Valeria,
Hopf Henning
Publication year - 1998
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/(sici)1099-0682(199811)1998:11<1733::aid-ejic1733>3.0.co;2-h
Subject(s) - chemistry , silylation , trimethylsilyl , electrophile , diastereomer , group 2 organometallic chemistry , organometallic chemistry , reagent , monomer , polymer chemistry , lithium (medication) , medicinal chemistry , organic chemistry , catalysis , molecule , polymer , medicine , endocrinology
Symmetrically 4,16‐disubstituted ( 3a–c ) and bridged ( 6a , b ) organometallic paracyclophane derivatives have been synthesized for use as monomeric precursors of organometallic poly‐ p ‐xylylenes. Both types of compounds were obtained by lithiation of the appropriately substituted paracyclophane bromides ( 1 or 4 ) and subsequent quenching of the resulting lithioparacyclophane derivatives with organometallic electrophiles. For the synthesis of 4,16‐bis(trimethylsilyl)[2.2]paracyclophane ( 3a ) we also examined the Grignard reaction, and as a result the first successful use of a 4,16‐bis Grignard reagent is described. According to the spectral data, the bridged compounds 6a, c are formed as diastereomeric mixtures of a meso‐ and a d,l form. The diastereomers were separated by fractional recrystallization and characterized.