Synthesis of novel carborane-containing terminal alkynes

I. D. Kosenko; N. V. Dudarova; I. V. Ananyev; V. I. Bregadze; A. A. Semioshkin

doi:10.1007/s11172-018-2100-0

Synthesis of novel carborane-containing terminal alkynes

Authors: Kosenko I.D.¹, Dudarova N.V.¹, Ananyev I.V.¹, Bregadze V.I.¹, Semioshkin A.A.¹
Affiliations:
1. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences
Issue: Vol 67, No 3 (2018)
Pages: 500-503
Section: Full Articles
URL: https://journals.rcsi.science/1066-5285/article/view/242330
DOI: https://doi.org/10.1007/s11172-018-2100-0
ID: 242330

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Abstract

Lithiation of 1-bromomethyl-o-carborane with lithium diisopropylamide (LDA) in THF results in the in situ formation of 1-lithio-2-bromomethyl-o-carborane, the reaction of which with 3-trimethylsilylprop-2-ynal gives 2-(2-trimethylsilylethynyl)-3,4-(о-carborano)-2,5-dihydrofuran. Subsequent base-catalyzed desilylation furnishes new terminal alkynes of closoand nido-carborane series.