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Synthesis and Molecular Structure of Silole Derivatives Bearing Functional Groups on Silicon: 1,1‐Organoboration of Dialkynylsilanes
Author(s) -
Khan Ezzat,
Bayer Stefan,
Kempe Rhett,
Wrackmeyer Bernd
Publication year - 2009
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/ejic.200900697
Subject(s) - chemistry , intramolecular force , nonane , triethylborane , acetic acid , ring (chemistry) , intermolecular force , silicon , derivative (finance) , nuclear magnetic resonance spectroscopy , medicinal chemistry , stereochemistry , molecule , organic chemistry , financial economics , economics , catalysis
Various dialkynylsilanes bearing Si–H or SiCl functions in addition to the alkynyl groups react with an excess of triethylborane after heating at 100–110 °C for several days via slow intermolecular 1,1‐ethylboration followed by fast intramolecular 1,1‐vinylboration to give Si‐functional substituted siloles. Similarly, the reactions with 9‐ethyl‐9‐borabicyclo[3.3.1]nonane afford polycyclic compounds containing the silole ring. Protodeborylaton with an excess of acetic acid leads to simultaneous substitution of BEt 2 and Si–H functions to give 1‐acetoxysiloles. All new siloles were characterized by NMR spectroscopy in solution ( 1 H, 11 B, 13 C, 29 Si NMR), and for one example of a polycyclic silole derivative the molecular structure was determined by X‐ray analysis.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)