33241-82-6Relevant academic research and scientific papers
Highly syn selective addition of aqueous HBr to hydrophobically shielded arylalkynes
Knorr, Rudolf,Rossmann, Eva C.,Knittl, Monika,B?hrer, Petra
, p. 5332 - 5338 (2014/07/08)
Hydrophobically shielded alkynes HC≡C-aryl, carrying 2,6-di- and 2,4,6-tri-tert-butylphenyl as the aryl group, can add aqueous HBr on heating in moist chloroform solutions to produce pure H2C=C(-Br)-aryl (isolated yields 96%, no hydrolysis). Em
Highly syn selective addition of aqueous HBr to hydrophobically shielded arylalkynes
Knorr, Rudolf,Rossmann, Eva C.,Knittl, Monika,B?hrer, Petra
, p. 5332 - 5338 (2014/12/10)
Hydrophobically shielded alkynes HCC-aryl, carrying 2,6-di- and 2,4,6-tri-tert-butylphenyl as the aryl group, can add aqueous HBr on heating in moist chloroform solutions to produce pure H2CC(-Br)-aryl (isolated yields 96%, no hydrolysis). Employment of DCC-aryl furnished initially only the E stereoisomer of DHCC(-Br)-aryl (stereospecific syn addition), which was slowly both dedeuteriated and partially transformed to the Z stereoisomer by HBr. The strongly retarded HBr addition to H3C-CC-aryl in moist chloroform produced again more E than Z product, whereas a thermodynamic E/Z ratio of 10:87 was found in moist acetic acid. Substitution of Br by LiSnMe3produced H2CC(-SnMe3)-aryl with well resolved long range 119Sn NMR coupling constants.
Reactions of (2,4,6-Tri-t-butyl)thiobenzaldehyde with Diazo Compounds. Synthesis and Reactions of Sterically Congested Thiiranes
Watanabe, Soichiro,Kawashima, Takayuki,Tokitoh, Norihiro,Okazaki, Renji
, p. 1437 - 1448 (2007/10/02)
Sterically congested thiiranes having a 2,4,6-tri-t-butylphenyl group were synthesized by the reactions of (2,4,6-tri-t-butyl)thiobenzaldehyde with sterically hindered diazo compounds.Thermal desulfurization of the most congested thiirane, 2,2-di-t-butyl-3-(2,4,6-tri-t-butylphenyl)thiirane (15c), did not proceed even upon using highly reactive reagents, such as hexamethylphosphorous triamide or organolithiums.The photoreaction of 15c did not give the corresponding styrene, but afforded several products containing 2,4,6-tri-t-butylbenzothiophene and Dewar benzenes,2,2-di-t-butyl-3-(3,4,6-tri-t-butylbicyclohexa-2,5-dien-2-yl)thiirane and 2-t-butyl-3,3-dimethyl-1-(1,3,5-tri-t-butylbicyclohexa-2,5-diene-2-yl)-1-butene (24), the latter of which is the first example for a vinyl-substituted Dewar benzene.Compound 24 has a unique reactivity, giving a rearrangement product, 2-t-butyl-3,3-dimethyl-1-(1,3,5-tri-t-butylbicyclohexa-2,5-diene-2-yl)-1-butene on thermolysis.
