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Volumn 73, Issue 6, 2008, Pages 2432-2434

Synthesis of cyclic thioethers through tandem C(sp3)-S and C(sp2)-S bond formations from α,β′-dichloro vinyl ketones

Author keywords

[No Author keywords available]

Indexed keywords

ACIDS; CHEMICAL BONDS; FRIEDEL-CRAFTS REACTION; KETONES; SYNTHESIS (CHEMICAL);

EID: 41849094117     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo702457t     Document Type: Article
Times cited : (29)

References (35)
  • 7
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    • Oh, K. Org. Lett. 2007, 9, 2973.
    • (2007) Org. Lett , vol.9 , pp. 2973
    • Oh, K.1
  • 13
    • 33744998155 scopus 로고    scopus 로고
    • Selecteted thiopyran-4-one examples, see: (f) Rosiak, A.; Christoffers, J. Tetrahedron Lett. 2006, 47, 5095.
    • Selecteted thiopyran-4-one examples, see: (f) Rosiak, A.; Christoffers, J. Tetrahedron Lett. 2006, 47, 5095.
  • 20
    • 0037163266 scopus 로고    scopus 로고
    • Selected benzo[b]thiepinone derivatives, see: (m) Bendorf, H. D.; Colella, C. M.; Dixon, E. C.; Marchetti, M.; Matukonis, A. N.; Musselman, J. D.; Tiley, T. A. Tetrahedron Lett. 2002, 43, 7031.
    • Selected benzo[b]thiepinone derivatives, see: (m) Bendorf, H. D.; Colella, C. M.; Dixon, E. C.; Marchetti, M.; Matukonis, A. N.; Musselman, J. D.; Tiley, T. A. Tetrahedron Lett. 2002, 43, 7031.
  • 24
    • 0010915254 scopus 로고
    • Assignment of alkene geometry by NMR, see
    • Assignment of alkene geometry by NMR, see: Martens, H.; Hooranaert, G.; Toppet, S. Tetrahedron 1973, 29, 4241.
    • (1973) Tetrahedron , vol.29 , pp. 4241
    • Martens, H.1    Hooranaert, G.2    Toppet, S.3
  • 25
    • 0000835020 scopus 로고    scopus 로고
    • Capon, B.; Kwok, F-C. J. Am. Chem. Soc. 1989, 111, 5346. 2-Methyl thiophen-3-ones 4b, 4g, and 4l rapidly decomposed at ambient temperature over 1-24 h, and thus are isolated as their O-acetyl thiophene derivatives, see the Supporting Information.
    • Capon, B.; Kwok, F-C. J. Am. Chem. Soc. 1989, 111, 5346. 2-Methyl thiophen-3-ones 4b, 4g, and 4l rapidly decomposed at ambient temperature over 1-24 h, and thus are isolated as their O-acetyl thiophene derivatives, see the Supporting Information.
  • 26
    • 41849106383 scopus 로고    scopus 로고
    • cis- and trans-Chloro vinyl ketones 3a undergo cyclization, respectively, thus a mixture of stereoisomers was employed in all other substrates 3b-o.
    • cis- and trans-Chloro vinyl ketones 3a undergo cyclization, respectively, thus a mixture of stereoisomers was employed in all other substrates 3b-o.
  • 27
    • 41849135339 scopus 로고    scopus 로고
    • α′-Methyl-substituted β-chloro vinyl ketones 3b, 3g, and 3l are expected to enhance the competition between Michael reaction and alkylation due to the steric hinderance of a methyl group.
    • α′-Methyl-substituted β-chloro vinyl ketones 3b, 3g, and 3l are expected to enhance the competition between Michael reaction and alkylation due to the steric hinderance of a methyl group.
  • 28
    • 41849098039 scopus 로고    scopus 로고
    • We are currently investigating the synthesis of β-keto thioketone of 7 to confirm the possibility of crossover between 5 and 8, or 6 and 7
    • We are currently investigating the synthesis of β-keto thioketone of 7 to confirm the possibility of crossover between 5 and 8, or 6 and 7.
  • 30
    • 41849083368 scopus 로고    scopus 로고
    • Oxidative S-S coupling of 7 followed by intramolecular alkylation to 9 cannot be ruled out.
    • Oxidative S-S coupling of 7 followed by intramolecular alkylation to 9 cannot be ruled out.
  • 34
    • 41849115500 scopus 로고    scopus 로고
    • 2O conditions, no reaction was observed.
    • 2O conditions, no reaction was observed.
  • 35
    • 34547172676 scopus 로고    scopus 로고
    • and references cited therein. Sulfone analogues for cell imaging application, see
    • Sulfone analogues for cell imaging application, see: Toutchkine, A.; Nguyen, D.; Hahn, K. M. Org. Lett. 2007, 9, 2775 and references cited therein.
    • (2007) Org. Lett , vol.9 , pp. 2775
    • Toutchkine, A.1    Nguyen, D.2    Hahn, K.M.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.