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Volumn 61, Issue 20, 1996, Pages 6783-6789

Radical sequential processes promoted by 1,5-radical translocation reaction: Formation and [3 + 2] anulation of alkenesulfanyl radicals

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EID: 0009725984     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960279v     Document Type: Article
Times cited : (45)

References (39)
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    • The term of "radical traslocation" has been introduced by Curran. Radicals are generated at favorable sites and then "traslocated" to new sites. See: Curran, D. P.; Kim, D.; Liu, H. T:; Shen, W. J. Am. Chem. Soc. 1988, 110, 5900.
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    • (a) Curran, D. P. Radical addition reactions. In Comprehensive Organic Synthesis; Pergamom Press: Oxford, U.K., 1991; Vol. 4, Chapter 4.2.
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    • Baciocchi, E.; Muraglia, E. Tetrahedron Lett. 1993, 34, 5015. Ichinose, Y.; Wakamatsu, K.; Nazaki, K.; Birbaum, J-L; Oshima, K.; Utimoto, K. Chem. Lett. 1987, 1647.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 5015
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    • Radical addition reactions
    • Pergamon Press: Oxford, U.K., Chapter 4.1.4.3
    • Curran, D. P. Radical addition reactions. In Comprehensive Organic Synthesis; Pergamon Press: Oxford, U.K., 1991; Vol. 4, Chapter 4.1.4.3. Giese, B. Angew. Chem., Int. Ed. Engl. 1983, 22, 753.
    • (1991) Comprehensive Organic Synthesis , vol.4
    • Curran, D.P.1
  • 18
    • 0001728539 scopus 로고
    • Curran, D. P. Radical addition reactions. In Comprehensive Organic Synthesis; Pergamon Press: Oxford, U.K., 1991; Vol. 4, Chapter 4.1.4.3. Giese, B. Angew. Chem., Int. Ed. Engl. 1983, 22, 753.
    • (1983) Angew. Chem., Int. Ed. Engl. , vol.22 , pp. 753
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    • Giese, B. Angew. Chem., Int. Ed. Engl. 1989, 28, 969. Giese, B; Lachein, S., Angew. Chem., Int. Ed. Engl. 1982, 21, 768. Singer, L. A.; Chen, J., Tetrahedron Lett. 1969, 4849.
    • (1989) Angew. Chem., Int. Ed. Engl. , vol.28 , pp. 969
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    • 84985609343 scopus 로고
    • Giese, B. Angew. Chem., Int. Ed. Engl. 1989, 28, 969. Giese, B; Lachein, S., Angew. Chem., Int. Ed. Engl. 1982, 21, 768. Singer, L. A.; Chen, J., Tetrahedron Lett. 1969, 4849.
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    • Giese, B.1    Lachein, S.2
  • 27
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    • (1969) Tetrahedron Lett. , pp. 4849
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    • Free Radical Addition involving C-C triple bonds
    • Patai, S., Ed.; J. Wiley: New York, Chapter 16
    • It is generally accepted that steric hindrance between radical scavenger and the substituent cis to the radical center is an important effect in determining the stereochemistry of radical addition of thiols to alkynes (refs 6a,d; see also: Chatgilialoglu, C.; Ferreri, C. Free Radical Addition involving C-C triple bonds. In The Chemistry of Triple-bonded Functional Groups; Patai, S., Ed.; J. Wiley: New York, 1994; Suppl. C2, Vol. 2, Chapter 16.
    • (1994) The Chemistry of Triple-bonded Functional Groups , vol.2 , Issue.2 SUPPL. C
    • Chatgilialoglu, C.1    Ferreri, C.2
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    • note
    • Dialkylacetylenes undergo radical addition of benzenethiol leading to (Z) and (E)-adducts in a Z/E ratio increasing with the size of alkyl substituents (refs 6a,e). The predominant formation of transaddition (Z)-products with hex-3-yne and oct-4-yne would result from predominant occurrence of (Z)-radicals in the mixture of equilibrating GZ)- and (E)-radicals, owing to steric hindrance between the alkyl substituents.
  • 38
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    • (1989) Chem. Abstr. , vol.111
  • 39
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    • note
    • The source of these products is still unclear. A study of carbon-centered radical addition to the alkyne triple bond is in progress.


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