2014
DOI: 10.1002/cctc.201400005
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Titanium(salen)‐Catalysed Synthesis of Di‐ and Trithiocarbonates from Epoxides and Carbon Disulfide

Abstract: The combination of a bimetallic titanium(salen) complex [Ti(salen)O]2 and either tetrabutylammonium bromide or tributylamine forms a highly active catalyst system for the reaction between epoxides and carbon disulfide to lead to di‐ and/or trithiocarbonates. Reactions can be performed at 90 °C by using just 0.5–1.0 mol % of the catalysts. The reactions proceed with the inversion of the epoxide configuration and on the basis of kinetic and spectroscopic evidence, a mechanism to account for the results is propos… Show more

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Cited by 30 publications
(28 citation statements)
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References 97 publications
(10 reference statements)
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“…52,62,63 Finally, we turned our attention to the conversion of internal epoxides 1p-u (Table 3). 52,62,63 Finally, we turned our attention to the conversion of internal epoxides 1p-u (Table 3).…”
Section: Resultsmentioning
confidence: 99%
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“…52,62,63 Finally, we turned our attention to the conversion of internal epoxides 1p-u (Table 3). 52,62,63 Finally, we turned our attention to the conversion of internal epoxides 1p-u (Table 3).…”
Section: Resultsmentioning
confidence: 99%
“…We suggest the in situ formation of adduct 9 by the addition of LiO t Bu to CS 2 in the initial step. 46,52,58 Subsequently, a nucleophilic attack at the sterically less hindered β-position of epoxide 1 by the xanthogenate 9 led to 10. 4E).…”
Section: Resultsmentioning
confidence: 99%
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“…Although CS2 is an isoelectronic heterocumulene of carbon dioxide, its reaction with epoxides has been much less explored. The reaction results, in most cases, in a mixture of the 1,3-oxathiolane-2-thione and 1,3-dithiolan-2-thione as well as in 1,3-dithiolane-2ones, 1,3-oxathiolane-2-ones, 1,3-dioxolane-2-thiones and thiiranes [102][103][104]; therefore, good functional group selectivity is the most important goal to achieve in this process. The same catalytic system optimized for the carboxylation of epoxides was tested in the thiocarboxylation variant with a minimum amount of CS2.…”
Section: A C C E P T Ementioning
confidence: 99%
“…Even more recently, the same group used a Ti(IV)-salen-based catalyst at somewhat higher temperatures (90 °C) but employing much lower (co)catalyst loadings (1 mol%) [139]. Even more recently, the same group used a Ti(IV)-salen-based catalyst at somewhat higher temperatures (90 °C) but employing much lower (co)catalyst loadings (1 mol%) [139].…”
Section: Related Heterocycles Incorporating Co 2 or Related Synthonsmentioning
confidence: 99%