23604-62-8Relevant academic research and scientific papers
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
Thio- and dithioesters as dipolarophiles in reactions with thiocarbonyl ylides
Urbaniak, Katarzyna,Mloston, Grzegorz,Gulea, Mihaela,Masson, Serge,Linden, Anthony,Heimgartner, Heinz
, p. 1604 - 1612 (2005)
The thiocarbonyl S-methylldes 3a-c, generated in situ by thermal decomposition of the corresponding 2,5-dihydro-1,3,4-thiadiazoles, undergo [3+2] cycloadditions with diphenyl trithiocarbonate (5a) to give 1,3-dithiolanes. The regloselectivity of the reaction of the cycloaliphatic dipoles 3b and 3c is reversed in comparison with that of the aromatic 3a. A mixture of both regioisomeric cycloadducts is formed in the reaction between 3b and methyl dithiobenzoate (6a), whereas only one regioisomer is obtained with thiophthalide (7). Dialkyl phosphonodithioformates 8 are shown to be efficient C=S dipolarophiles in reactions with thiocarbonyl S-methylides 3a-3d, affording 1,3-dithiolane-4-phosphonates. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.
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.
Trapping of a thiocarbonyl ylide with imidazolethiones, pyrimidinethione, and thioamides
Mloston, Grzegorz,Gendek, Tomasz,Linden, Anthony,Heimgartner, Heinz
, p. 290 - 296 (2007/10/03)
The reactions of 1,1,3,3-tetramethyl-8-thia-5,6-diazaspirol[3.4]oct-5- en-2-one (1a) with imidazole-2-thiones 3 and pyrimidine-2(1H)-thione (6) in CHCl3 at 40-50°yield 2,2,4,4-tetramethylcyclobutanone dithioacetals of type 4 and 7, respectively
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
