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Umsetzungen von Metall- und Metalloidverbindungen mit mehrfunktionellen Molekuelen, XXXIII. Zur Reaktion von Propargylaminen bzw. N-Organyl-N-(trimethylsilyl)propargylaminen mit Bor-Halogen- bzw. Bor-Schwefel-Verbindungen
Meller, Anton,Hirninger, Franz J.,Noltemeyer, Mathias,Maringgele, Walter
, p. 2519 - 2535 (2007/10/02)
The N-organyl-N-(trimethylsilyl)propargylamines 1 - 5 are obtained from N-organylpropargylamines with chlorotrimethylsilane and triethylamine.The reaction of 1 - 5 with halogenoboranes, organylhalogenoboranes, or methylbis(methylthio)borane leads to the (organylpropargylamino)boranes 6 - 13.On the other hand, in the reaction of N-organylpropargylamines with halogenoboranes the C C triple bond inserts into the halogen-boron bond and yields the 1-azonia-2-borata-3-cyclopentene system 14 - 19 by intramolecular coordination.N-Organyl-N-(trimethylsilyl)propargylamines react with bromodimethylborane in the molar ratio 1 : 2 under elimination of trimethylborane to give the 1-aza-2-bora-3-cyclopentene ring system 20 - 24.In the reaction of N-organyldipropargylamines with halogenoboranes both C C triple bonds insert into boron-halogen bonds to form the 1-azonia-5-boratabicycloocta-3,6-diene system 25 - 38.Tripropargylamine reacts with trichloro- and tribromoborane under three-fold insertion and intramolecular coordination to yield the 3,7,10-trihalogeno-1-azonia-5-boratatricyclo1,5>undeca-3,6,10-trienes 39 and 40.For 39 the X-ray structure is reported.