Lithium alkyl assisted coupling of a 2-cyano-2,3-dihydro-1H-1,3,2-diazaborole to give (BuNCH)-Bu-t=CHN(Bu-t)BC(Pr-i)=N-BN(Bu-t)CH=(CHNBu)-Bu-t

Weber L, Domke I, Rausch A, Chrostowska A, Dargelos A (2004)
Journal of the Chemical Society. Dalton Transactions (14): 2188-2191.

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Reaction of 2-cyano-1,3,2-diazaborole (BuNCH)-Bu-t=CHN(Bu-t)BCN (2) with half an equivalent of isopropyllithium afforded compound (BuNCH)-Bu-t=CHN(Bu-t)BC(Pr-i)=N-BN(Bu-t)CH=(CHNBu)-Bu-t (7). In contrast to this, a 1:1 stoichiometry of the reactants led to (BuNCH)-Bu-t=CHN(Bu-t)(BPr)-Pr-i ( 6) as the product of a nucleophilic substitution process at the boron atom. Similarly, regardless of the molar ratio of reactants employed, treatment of 2 with cyclopropyllithium, isobutyllithium or phenyllithium afforded solely substitution products (BuNCH)-Bu-t=CHN(Bu-t)BR. [R=cPr (12); Ph (13); Bu-i (14)].
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Weber L, Domke I, Rausch A, Chrostowska A, Dargelos A. Lithium alkyl assisted coupling of a 2-cyano-2,3-dihydro-1H-1,3,2-diazaborole to give (BuNCH)-Bu-t=CHN(Bu-t)BC(Pr-i)=N-BN(Bu-t)CH=(CHNBu)-Bu-t. Journal of the Chemical Society. Dalton Transactions. 2004;(14):2188-2191.
Weber, L., Domke, I., Rausch, A., Chrostowska, A., & Dargelos, A. (2004). Lithium alkyl assisted coupling of a 2-cyano-2,3-dihydro-1H-1,3,2-diazaborole to give (BuNCH)-Bu-t=CHN(Bu-t)BC(Pr-i)=N-BN(Bu-t)CH=(CHNBu)-Bu-t. Journal of the Chemical Society. Dalton Transactions(14), 2188-2191.
Weber, L., Domke, I., Rausch, A., Chrostowska, A., and Dargelos, A. (2004). Lithium alkyl assisted coupling of a 2-cyano-2,3-dihydro-1H-1,3,2-diazaborole to give (BuNCH)-Bu-t=CHN(Bu-t)BC(Pr-i)=N-BN(Bu-t)CH=(CHNBu)-Bu-t. Journal of the Chemical Society. Dalton Transactions, 2188-2191.
Weber, L., et al., 2004. Lithium alkyl assisted coupling of a 2-cyano-2,3-dihydro-1H-1,3,2-diazaborole to give (BuNCH)-Bu-t=CHN(Bu-t)BC(Pr-i)=N-BN(Bu-t)CH=(CHNBu)-Bu-t. Journal of the Chemical Society. Dalton Transactions, (14), p 2188-2191.
L. Weber, et al., “Lithium alkyl assisted coupling of a 2-cyano-2,3-dihydro-1H-1,3,2-diazaborole to give (BuNCH)-Bu-t=CHN(Bu-t)BC(Pr-i)=N-BN(Bu-t)CH=(CHNBu)-Bu-t”, Journal of the Chemical Society. Dalton Transactions, 2004, pp. 2188-2191.
Weber, L., Domke, I., Rausch, A., Chrostowska, A., Dargelos, A.: Lithium alkyl assisted coupling of a 2-cyano-2,3-dihydro-1H-1,3,2-diazaborole to give (BuNCH)-Bu-t=CHN(Bu-t)BC(Pr-i)=N-BN(Bu-t)CH=(CHNBu)-Bu-t. Journal of the Chemical Society. Dalton Transactions. 2188-2191 (2004).
Weber, Lothar, Domke, Imme, Rausch, Andreas, Chrostowska, Anna, and Dargelos, Alain. “Lithium alkyl assisted coupling of a 2-cyano-2,3-dihydro-1H-1,3,2-diazaborole to give (BuNCH)-Bu-t=CHN(Bu-t)BC(Pr-i)=N-BN(Bu-t)CH=(CHNBu)-Bu-t”. Journal of the Chemical Society. Dalton Transactions 14 (2004): 2188-2191.
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1,3,2-Diazaborolyl-functionalized thiophenes and dithiophenes: synthesis, structure, electrochemistry and luminescence.
Weber L, Werner V, Domke I, Stammler HG, Neumann B., Dalton Trans (31), 2006
PMID: 16883404

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