23604-62-8Relevant articles and documents
Strong influence of the trifluoromethyl group on the chemoselectivity of [3+2]-cycloadditions of thiocarbonyl S-methanides with α,β-unsaturated ketones
Mlostoń, Grzegorz,Grzelak, Paulina,Heimgartner, Heinz
, p. 56 - 60 (2016)
The in situ-generated reactive thiocarbonyl S-methanides were reacted with fluorinated enones. The type of the obtained [3+2]-cycloadduct depends strongly on the location of the activating CF3group. In the case of enones containing the CF3
Interception of an Intermediate Thiocarbonyl Ylide by NH-Compounds
Mloston,Janicka,Woznicka,Linden,Heimgartner
, p. 1805 - 1817 (2007/10/03)
By thermal decomposition of 1,1,3,3-tetramethyl-5-thia-7,8-diazaspiro[3.4] octan2-one (1), 2,2,4,4-tetramethyl-3-thioxocyclobutanone S-methylide (2) was generated as an intermediate. This reactive "thiocarbonyl ylide" was trapped by protic agents such as alcohols, NH- and SH-acidic compounds to give 1,3-adducts of the acetal type. In a mixture of methanol and ammonia, the spiroheterocycle 1 was deprotonated and competitive ring opening of the 2,5-dihydro-1,3,4-thiadiazole and the cyclobutane ring occurred to give the hydrazono derivative 7 and the 1,3,4-thiadiazole 8, respectively. Surprisingly, 2 was intercepted by maleimide in a 1,3-dipolar cycloaddition.
Can polymerization trap intermediates in 1,3-dipolar cycloadditions?
Huisgen, Rolf,Penelle, Jacques,Mloston, Grzegorz,Padias, Anne Buyle,Hall Jr.
, p. 266 - 274 (2007/10/02)
2,2,4,4-Tetramethyl-3-thioxocyclobutanone 5-methylide (TTCM) is a nucleophilic 1,3-dipole which is known to undergo two-step cycloadditions to very electron poor olefins. When this 1,3-dipole is generated from its precursor, the 1,3,4-thiadiazoline 7, in
