Dimethyl 3,4,5,5-tetraphenyl-1,3-thiazolidine-2,2-dicarboxylate and 3,3-dichloro-2,2,4,4,3′-pentamethyl-<i>r</i>-2′,<i>t</i>-4′-diphenylcyclobutane-1-spiro-5′-1,3-thiazolidine

Domagała, Małgorzata; Palusiak, Marcin; Pfitzner, Arno; Zabel, Manfred; Urbaniak, Katarzyna; Mlostoń, Grzegorz; Grabowski, Sławomir J.

doi:10.1107/s0108270104015045

Cited by 2 publications

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“…Chromatographic separation of the mixture yielded two products in a ratio that was dependent upon the concentration of the reactants. This conclusion was confirmed by an X-ray crystal-structure determination [28]. [28]).…”

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Mlostoń

Urbaniak

Linden

et al. 2002

HCA

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Dedicated to Professor Albert Padwa on the occasion of this 60th birthayThe reaction of 2,2,4,4-tetramethyl-3-thioxocyclobutanone (1) with cis-1-alkyl-2,3-diphenylaziridines 5 in boiling toluene yielded the expected trans-configured spirocyclic 1,3-thiazolidines 6 (Scheme 1). Analogously, dimethyl trans-1-(4-methoxyphenyl)aziridine-2,3-dicarboxylate (trans-7) reacted with 1 and the corresponding dithione 2, respectively, to give spirocyclic 1,3-thiazolidine-2,4-dicarboxylates 8 (Scheme 2). However, mixtures of cis-and trans-derivatives were obtained in these cases. Unexpectedly, the reaction of 1 with dimethyl 1,3diphenylaziridine-2,2-dicarboxylate (11) led to a mixture of the cycloadduct 13 and 5-(isopropylidene)-4phenyl-1,3-thiazolidine-2,2-dicarboxylate (14), a formal cycloadduct of azomethine ylide 12 with dimethylthioketene (Scheme 3). The regioisomeric adduct 16 was obtained from the reaction between 2 and 11. The structures of 6b, cis-8a, cis-8b, 10, and 16 have been established by X-ray crystallography.

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“…When the reaction with 1 was carried out in boiling xylene for 60 h, leading to the formation of the intermediate azomethine ylide 12, no 1 remained according to TLC analysis. [28]). 3 ) The more polar crystalline product 13 (6%) was the expected [3 2] cycloadduct (cf.…”

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Mlostoń

Urbaniak

Linden

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“…[22][23][24]). Thermolysis of cis-1-methyl-2,3-diphenylaziridine (22) in boiling toluene in the presence of 4b afforded a single product whose structure was again established by X-ray crystallography [25] (Scheme 7). In accordance with the expected reaction course, the Ph groups are trans oriented, i.e., the intermediate 1,3-dipole 23 has been generated by a conrotatory ring opening of 22.…”

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Synthesis and Reactions of a New Cyclobutanethione Derivative

Mlostoń

Majchrzak

Rutkowska

et al. 2005

Helvetica Chimica Acta

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The 3,3-dichloro-2,2,4,4-tetramethylcyclobutanethione (4b) was prepared from the parent diketone by successive reaction with PCl5 and Lawesson reagent in pyridine. This new thioketone 4b was transformed into 1-chlorocyclobutanesulfanyl chloride 5 and chloro 1-chlorocyclobutyl disulfide 9 by treatment with PCl5 and SCl2, respectively, in chlorinated solvents (Schemes 1 and 2). These products reacted with S-and P-nucleophiles by substitution of Cl− at the S-atom; e.g., the reaction with 4b yielded the diand trisulfides 6b and 11, respectively. Surprisingly, only pentasulfide 12 was formed in the reaction of 9 with thiobenzophenone (Scheme 3). In contrast to 5 and 9, the corresponding chloro 1-chlorocyclobutyl trisulfide 13 could not be detected, but reacted immediately with the starting thioketone 4b to give the tetrasulfide 14 (Scheme 4). Oxidation of 4b with 3-chloroperbenzoic acid (mCPBA) yielded the corresponding thione oxides (= sulfine) 15, which underwent 1,3-dipolar cycloadditions with thioketones 3a and 4b (Scheme 5). Furthermore, 4b was shown to be a good dipolarophile in reactions with thiocarbonylium methanides (Scheme 6) and iminium ylides (= azomethine ylides; Scheme 7). In the case of phenyl azide, the reaction with 4b gave the symmetrical trithiolane 25 (Scheme 8). and 2). These products reacted with S-and P-nucleophiles by substitution of Cl -at the sulfanyl group; e.g. the reaction with 4b yielded the di-and trisulfane derivatives 6b and 11, respectively. Surprisingly, only pentasulfane 12 was formed in the reaction of 9 with thiobenzophenone (Scheme 3). In contrast to 5 and 9, the corresponding α-chloro trisulfanylchloride 13 could not be detected, but reacted immediately with the starting thioketone 4b togive the tetrasulfane 14 (Scheme 4). Oxidation of 4b with mCPBA yielded the corresponding sulfine 15, which underwent 1,3-dipolar cycloadditions with thioketones 3a and 4b (Scheme 5). Furthermore, 4b has been shown to be a good dipolarophile in reactions with thiocarbonyl methanides and azomethine ylides (Schemes 6 and 7). In the case of phenyl azide, the reaction with 4b gave the symmetrical trithiolane 25 (Scheme 8).

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Dimethyl 3,4,5,5-tetraphenyl-1,3-thiazolidine-2,2-dicarboxylate and 3,3-dichloro-2,2,4,4,3′-pentamethyl-r-2′,t-4′-diphenylcyclobutane-1-spiro-5′-1,3-thiazolidine

Cited by 2 publications

References 22 publications

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Synthesis and Reactions of a New Cyclobutanethione Derivative

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