27471-13-2Relevant academic research and scientific papers
Pd-catalysed reactions of alkynes with model distannanes and poly[di-(n-butyl)]stannane
Khan, Aman,Lough, Alan J.,Gossage, Robert A.,Foucher, Daniel A.
, p. 2469 - 2476 (2013/03/13)
A reinvestigation of Pd-catalysed alkyne (R′-C≡CH; R′ = H, Ph) insertion chemistry involving R3SnSnR3 (3a: R = Me; 3b: R = n-Bu) was undertaken. Model distannyl ethylenes 4a-b (Me 3SnCHCR′SnMe3) and 5a-b ((n-Bu) 3SnCHCR′Sn(n-Bu)3) were reproduced and further characterized by NMR (119Sn, 13C, 1H) and UV-Vis spectroscopy. In the presence of an excess of phenylacetylene, dimerization-carbostannylation of compound 4b yielded the new conjugated butadiene, (Z,Z)-1,4-bis(trimethylstannyl)-1,4-diphenyl-buta-1,3-diene (9). An X-ray structure determination of 9 reveals a symmetrical double-bond Z confirmation. Compound 9 was further characterized by NMR, UV-Vis spectroscopy, and MS. A DFT analysis of model compounds (4a-b, 5a-b, 9) and the experimental and theoretical λmax values from the UV-Vis spectra were also compared. Acetylene and phenylacetylene Pd-catalysed insertion into the backbone of poly[di-(n-butyl)]stannane 12 resulted in new, modest molecular weight, partially inserted alkene tin polymers (13a-b) that were also characterized by GPC, NMR, UV-Vis spectroscopy and elemental analysis.
Copper-catalyzed distannylation of alkynes
Yoshida, Hiroto,Shinke, Ayako,Takaki, Ken
supporting information, p. 11671 - 11673 (2013/12/04)
A copper(i)-phosphine complex has been found to facilely promote the distannylation of alkynes with the aid of a base, where a catalytically generated Cu-Sn species serves as a key intermediate. The broad versatility of the copper catalysis has been demonstrated by the facile distannylation of unfunctionalized aliphatic alkynes, being hardly achievable with the conventional palladium catalysts.
PALLADIUM CATALYSIS IN ORGANOTIN CHEMISTRY: ADDITION OF HEXAALKYLDITINS TO ALKYNES
Mitchell, T.N.,Amamria, A.,Killing, H.,Rutschow, D.
, p. 257 - 266 (2007/10/02)
Tetrakis(triphenylphosphine)palladium(0) catalyses the cis-addition of hexaalkylditins R6Sn2 (R = Me, Et, Bu) to acetylene and 1-alkynes; for R = Bu, however the reaction is not quantitative.With very few exceptions there is no reaction in the case of non
SYNTHESIS OF (Z)-1,2-BIS(TRIMETHYLSTANNYL)-1-ALKENES BY PLATINUM-CATALYSED ADDITION OF HEXAMETHYLDISTANNANE TO 1-ALKYNES
Mitchell, T. N.,Amamria, A.,Killing, H.,Rutschow, D.
, p. C45 - C47 (2007/10/02)
Addition of hexamethyldistannane to 1-alkynes in the presence of tetrakis(triphenylphosphine)palladium yields the title compounds, which can be photo-chemically isomerised to the corresponding (E)-distannylalkenes.
α-METALLATED VINYL CARBANIONOIDS. I. FORMATION OF α-STANNYLVINYL ANIONOIDS FROM 1,1-BIS(TRIMETHYLSTANNYL)ALKENES
Mitchell, T.N.,Amamria, A.
, p. 47 - 56 (2007/10/02)
Hydrostannation of 1-stannyl-1-alkynes leads to the formation of 1,1- and 1,2-distannyl-1-alkenes.The former can undergo lithiation (by alkyllithium in THF) with varying degrees of stereospecificity. 1,1-Dilithio-1-alkenes cannot be prepared by double lit
