Radical annulation: a method for preparation of carbocycles
Abstract
β-Acetylenic radicals, e.g., (6b) and (12), generated in three steps from epoxides or in two steps from α-halogenoketones, respectively, react with electron-deficient olefins to produce five-membered carbocycles by a process of conjugate addition and 5-exo-digonal closure.
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Direct radical addition reactions of thiocarbonyl (C=S) groups unaccompanied by β-scission have rarely been reported.
“Direct radical addition reactions of thiocarbonyl (C=S) groups unaccompanied by β-scission have rarely been reported despite their potential for constructing various sulfur-containing compounds.”
From Direct Radical Copolymerizations of Thioamides To Generate Vinyl Polymers with Degradable Thioether Bonds in the Backbones (2023) · cites this paper as [12]
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“In 12 − 16 This is most likely due to the instabilities of most thioaldehydes and thioketones in air 17 and favorable backward and β -scission reactions of the intermediate radicals formed from typical bench-stable thiocarbonyl compounds.”
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Hart, D. J., Krishnamurthy, R., Pook, L. M., et al. (1993) · Tetrahedron Letters · doi:10.1016/s0040-4039(00)61484-3 · Cited by 21 · see citing works
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Bowman, W. R., Brown, D. S., Burns, C. A., et al. (1992) · Tetrahedron · doi:10.1016/s0040-4020(01)89879-3 · Cited by 19 · see citing works
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Saičić, R. N., & Čeković, Ž. (1990) · Tetrahedron Letters · doi:10.1016/s0040-4039(00)97582-8 · Cited by 8 · see citing works
Chapter 2 Homolytic processes at sulfur
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Pottie, I. R., Crane, S. N., Gosse, A. L., et al. (2010) · Canadian Journal of Chemistry · doi:10.1139/v10-097 · Cited by 7 · see citing works
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Goulaouic-Dubois, C., Guggisberg, A., & Hesse, M. (1995) · Tetrahedron · doi:10.1016/0040-4020(95)00753-u · Cited by 7 · see citing works
Sano, R., Kudo, A., Tsubogo, T., et al. (2018) · Asian Journal of Organic Chemistry · doi:10.1002/ajoc.201800026 · Cited by 4 · see citing works
Srikrishna, A., & Reddy, T. J. (1996) · The Journal of Organic Chemistry · doi:10.1021/jo960423c · Cited by 4 · see citing works
Intermolecular Radical Addition Reactions
Togo, H. (2004) · Elsevier eBooks · doi:10.1016/b978-008044374-4/50005-0 · Cited by 3 · see citing works
Advances in Free Radical Reactions of Organoselenium and Organotellurium Compounds
Press, T. G. B. D. J. (2011) · Patai's chemistry of functional groups · doi:10.1002/9780470682531.pat0581 · Cited by 2 · see citing works
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Regan, A. C. (2005) · Elsevier eBooks · doi:10.1016/b0-08-044655-8/00012-x · Cited by 2 · see citing works
Mook, R., & Sher, P. M. (2003) · Organic Syntheses · doi:10.1002/0471264180.os066.11
ChemInform Abstract: RADICAL ANNULATION: A METHOD FOR PREPARATION OF CARBOCYCLES
ANGOH, A. G., & Clive, D. L. J. (1985) · ChemInform · doi:10.1002/chin.198545146
Self-citationLautens, M., Delanghe, P. H. M., & Long, M. S. (2007) · Encyclopedia of Reagents for Organic Synthesis · doi:10.1002/047084289x.ra036.pub2
(1995) · Elsevier eBooks · doi:10.1016/b0-08-044705-8/09009-9
Lautens, M., & Delanghe, P. H. M. (2001) · Encyclopedia of Reagents for Organic Synthesis · doi:10.1002/047084289x.ra036
Vasilchenko, D. S., Agafonova, A. V., Khlebnikov, A. F., Ростовский, Н. В., & Novikov, M. S. (2025) · Organic Chemistry Frontiers · doi:10.1039/d5qo01233c · Cited by 1 · see citing works
- Authors
- Gaëtan Angoh, A., & Clive, D. L. J.
- ORCID
- Clive, Derrick L. J.
- Venue
- J. Chem. Soc., Chem. Commun.
- Publisher
- Royal Society of Chemistry (RSC)
- Published
- 1985
- Volume
- 0
- Issue
- 14
- Pages
- 980-982
- ISSN
- 0022-4936 (ISSN-L)
- OpenAlex
- W2065561458
- Cited by
- 31
- References
- 0
- Citations by year
- 2025: 1 · 2023: 1 · 2020: 1 · 2018: 1 · 2012: 1
- FWCI
- 1.70
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Journal of the Chemical Society Chemical Communications (publishedVersion)
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Radical Photochemical Reactions
- Physical Sciences › Chemistry › Organic Chemistry › Organic Chemistry Synthesis Methods
- Physical Sciences › Chemistry › Organic Chemistry › Cyclopropane Reaction Mechanisms
- Keywords
- radical annulation, carbocycle synthesis, epoxides, electron-deficient olefins, conjugate addition, five-membered carbocycles
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