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A Facile Synthesis of Carbamoylsilanes, ‐boranes and ‐phosphane Oxides – Isolation of the First Uncomplexed Carbamoylborane
Author(s) -
Canac Yves,
Aniol Greg E.,
Conejero Salvador,
Donnadieu Bruno,
Bertrand Guy
Publication year - 2006
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.200600799
Subject(s) - chemistry , boranes , deprotonation , steric effects , chloride , organic chemistry , medicinal chemistry , combinatorial chemistry , ion , boron
C ‐(Trimethylsilyloxy)‐, C ‐(triisopropylsilyloxy)‐, C ‐(diphenylboryloxy), C ‐[bis(diisopropylamino)boryloxy]‐ and C ‐(di‐ tert ‐butylphosphoryloxy)‐ N , N ‐diisopropylaldiminium salts are readily prepared in good to excellent yields from either diisopropylformamide or (chloromethylene)diisopropylammonium chloride. Deprotonation of these aldiminium salts leads to transient (amino)(oxy)carbenes, which cleanly rearrange to carbamoyl derivatives. This synthetic methodology gives access to sterically hindered carbamoylsilanes, ‐boranes and phosphane oxides that are hardly accessible by other routes. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)