Developing nitrosocarborane chemistry

Dalton Transactions : an International Journal of Inorganic Chemistry
Samuel L PowleyAlan J Welch

Abstract

The new nitrosocarboranes [1-NO-2-R-1,2-closo-C2B10H10] [R = CH2Cl (1), CH3OCH2 (2) p-MeC6H4 (3), SiMe3 (4) and SiMe2tBu (5)] and [1-NO-7-Ph-1,7-closo-C2B10H10] (6) were synthesised by reaction of the appropriate lithiocarborane in diethyl ether with NOCl in petroleum ether followed by quenching the reaction with aqueous NaHCO3. These bright-blue compounds were characterised spectroscopically and, in several cases, crystallographically including structural determinations of 2 and 6 using crystals grown in situ on the diffractometer from liquid samples. In all cases the nitroso group bonds to the carborane as a 1e substituent (bent C–N–O sequence) and has little or no influence on <δ11B>, the weighted average 11B chemical shift, relative to that in the parent (monosubstituted) carborane. Mono- and dinitroso derivatives of 1,1′-bis(m-carborane), compounds 7 and 8 respectively, were similarly synthesised but attempts to prepare the mononitroso 1,1′-bis(o-carborane) by the same protocol led only to the hydroxylamine species [1-(1′-1′,2′-closo-C2B10H11)-2-N(H)OH-1,2-closo-C2B10H10] (9); the desired compound [1-(1′-1′,2′-closo-C2B10H11)-2-NO-1,2-closo-C2B10H10] (10) was only realised by switching to a non-aqueous work-up. The involve...Continue Reading

References

Aug 16, 2005·Chemical Society Reviews·Brian G Gowenlock, George B Richter-Addo
Nov 6, 2008·Chemical Communications : Chem Comm·Brian W HuttonAlan J Welch
Jun 12, 2010·Angewandte Chemie·David EllisAlan J Welch
Sep 11, 2010·Chemical Communications : Chem Comm·David EllisAlan J Welch
Sep 5, 2012·Dalton Transactions : an International Journal of Inorganic Chemistry·Amelia McAnawAlan J Welch
Sep 30, 2014·Angewandte Chemie·Wing Y ManAlan J Welch
Dec 30, 2014·Acta Crystallographica. Section A, Foundations and Advances·Luc J BourhisHorst Puschmann
Jan 2, 2015·Acta Crystallographica. Section E, Structure Reports Online·Wing Y ManAlan J Welch
Feb 24, 2015·Dalton Transactions : an International Journal of Inorganic Chemistry·Gobika ThiripuranatharAlan J Welch
Dec 15, 2015·Dalton Transactions : an International Journal of Inorganic Chemistry·Laura E RileyIgor B Sivaev

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Citations

Apr 6, 2017·Dalton Transactions : an International Journal of Inorganic Chemistry·Laura E RileyAlan J Welch
Jan 24, 2017·Dalton Transactions : an International Journal of Inorganic Chemistry·Gobika ThiripuranatharAlan J Welch
Feb 8, 2018·Chemistry : a European Journal·Daniel FranzShigeyoshi Inoue
Aug 28, 2021·Chemical Science·H D A Chathumal JayaweeraDmitry V Peryshkov

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