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Volumn 135, Issue 44, 2013, Pages 16610-16617

Radical cyclizations of cyclic ene sulfonamides occur with β-elimination of sulfonyl radicals to form polycyclic imines

Author keywords

[No Author keywords available]

Indexed keywords

ALDIMINES; CYCLIZATIONS; KETIMINES; RADICAL CYCLIZATIONS; SEVEN-MEMBERED RINGS;

EID: 84887679052     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja408387d     Document Type: Article
Times cited : (44)

References (68)
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    • 1 st ed. Renaud, P. Sibi, M. Wiley-VCH: Weinheim, Vol
    • Rosenstein, I. In Radicals in Organic Synthesis, 1 st ed.; Renaud, P.; Sibi, M., Eds.; Wiley-VCH: Weinheim, 2001; Vol 1, pp 50-71.
    • (2001) Radicals in Organic Synthesis , vol.1 , pp. 50-71
    • Rosenstein, I.1
  • 36
    • 0001174940 scopus 로고
    • Another possible outcome is that the sulfonyl radicals eventually dimerize. The products of such reactions would probably also react with tin hydrides. See: Chatgilialoglu, C.; Lunazzi, L.; Ingold, K. U. J. Org. Chem. 1983, 48, 3588-3589
    • (1983) J. Org. Chem. , vol.48 , pp. 3588-3589
    • Chatgilialoglu, C.1    Lunazzi, L.2    Ingold, K.U.3
  • 39
    • 84887726017 scopus 로고    scopus 로고
    • With 2 equiv of tin hydride, small amounts of starting material sometimes remained in pilot experiments, so we settled on 3 equiv for the preparative experiments.
    • With 2 equiv of tin hydride, small amounts of starting material sometimes remained in pilot experiments, so we settled on 3 equiv for the preparative experiments.
  • 40
    • 84887661975 scopus 로고    scopus 로고
    • Cyclization of the related 2-bromoacetamide analogue provided a crude spirocyclic imine product that was not stable to handling or isolation.
    • Cyclization of the related 2-bromoacetamide analogue provided a crude spirocyclic imine product that was not stable to handling or isolation.
  • 60
    • 84887720958 scopus 로고    scopus 로고
    • Ph.D. Thesis, University of Pittsburgh.
    • Zhang, H. Ph.D. Thesis, University of Pittsburgh, 2013.
    • (2013)
    • Zhang, H.1
  • 61
    • 0000568571 scopus 로고
    • This compound has been previously isolated and also described to be unstable. See: Burk, R. M.; Overman, L. E. Heterocycles 1993, 35, 205-225
    • (1993) Heterocycles , vol.35 , pp. 205-225
    • Burk, R.M.1    Overman, L.E.2
  • 67
    • 8144220624 scopus 로고
    • 4 th ed. Klamann, D. Hagemann, H. Georg Thieme Verlag: Stuttgart, Vol
    • Pawlenko, S. In Organic Nitrogen Compounds with a C,N-Double Bond, 4 th ed.; Klamann, D.; Hagemann, H., Eds.; Georg Thieme Verlag: Stuttgart, 1990; Vol E14b, pp 222-281.
    • (1990) Organic Nitrogen Compounds with A C,N-Double Bond , vol.14 , pp. 222-281
    • Pawlenko, S.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.