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The Chemistry of Stable Carbenes. Part 2. Benzoin‐type condensations of formaldehyde catalyzed by stable carbenes
Abstract
Stable carbenes derived from thiazole, 1 H‐imidazole, and 4 H‐1,2,4‐triazole are efficient catalysts for benzointype condensations of formaldehyde. Catalysts derived from N‐substituted thiazolium salts trimerize formaldehyde to dihydroxyacetone (II). Catalysts based on 1,4‐disubstituted 4 H‐1,2,4‐triazol‐1‐ium salts give glycolaldehyde (I) as the main product and no II, whereas N,N′‐disubstituted 1 H‐imidazol‐3‐ium salts yield mixtures of both products. The isolation of several intermediates in the catalytic cycle provide a better insight into the reaction mechanism.
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Cited by
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Kamber, N. E., Jeong, W., Waymouth, R. M., Pratt, R. C., Lohmeijer, B. G. G., & Hedrick, J. L. (2007) · Chemical Reviews · doi:10.1021/cr068415b · Cited by 1,489
A Brief Survey of Our Contribution to Stable Carbene Chemistry
Martin, D., Melaimi, M., Soleilhavoup, M., & Bertrand, G. (2011) · Organometallics · doi:10.1021/om200650x · Cited by 422
Zhukhovitskiy, A. V., MacLeod, M. J., & Johnson, J. A. (2015) · Chemical Reviews · doi:10.1021/acs.chemrev.5b00220 · Cited by 363
Metadata
- Authors
- Henrique Teles, J., Melder, J., Ebel, K., Schneider, R., Gehrer, E., Harder, W., Brode, S., Enders, D., Breuer, K., & Raabe, G.
- Venue
- Helvetica Chimica Acta
- Publisher
- Wiley
- Published
- 1996-02-07
- Volume
- 79
- Issue
- 1
- Pages
- 61-83
- ISSN
- 0018-019X (ISSN-L)
- 1522-2675
- OpenAlex
- W2162931609
- Cited by
- 188
- References
- 0
- FWCI
- 6.28
- Type
- journal article
- Language
- en
- Open access
- closed
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- CoChat. (2026). Citation check: The Chemistry of Stable Carbenes. Part 2. Benzoin‐type condensations of formaldehyde catalyzed by stable carbenes. https://app.cochat.ai/papers/10.1002/hlca.19960790108
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- Henrique Teles, J., Melder, J., Ebel, K., Schneider, R., Gehrer, E., Harder, W., Brode, S., Enders, D., Breuer, K., & Raabe, G. (1996). The Chemistry of Stable Carbenes. Part 2. Benzoin‐type condensations of formaldehyde catalyzed by stable carbenes. Helvetica Chimica Acta. https://doi.org/10.1002/hlca.19960790108
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