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Volumn 9, Issue 10, 2011, Pages 3780-3786

Radical carbonylation of ω-alkynylamines leading to α-methylene lactams. Synthetic scope and the mechanistic insights

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNYLS; AMINE NITROGEN; CARBONYL GROUPS; CYCLIZATION REACTIONS; DFT CALCULATION; HYDROGEN SHIFTS; LEAVING GROUPS; LONE PAIR; NUCLEOPHILIC ATTACK; RADICAL CARBONYLATION; RADICAL SPECIES; REACTION CONDITIONS; REACTION COURSE; REACTION MECHANISM; RING FORMATION; STABLE RADICALS; TIN HYDRIDES;

EID: 79955435660     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c1ob05145h     Document Type: Article
Times cited : (32)

References (51)
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    • Also see a review on acyl radicals:
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    • Ryu, I.1
  • 7
    • 0004269715 scopus 로고    scopus 로고
    • P. Renaud and M. P. Sibi, ed., Wiley-VCH: Weinheim
    • Radicals in Organic Synthesis, P. Renaud and M. P. Sibi, ed., Wiley-VCH: Weinheim, 2001, Vol. 1 and 2
    • (2001) Radicals in Organic Synthesis
  • 24
    • 40949156155 scopus 로고    scopus 로고
    • For tin radical mediated three-component reaction of alkynes, CO, and amines leading to α-unsaturated amides, see:
    • S. H. Kyne C. H. Schiesser H. Matsubara J. Org. Chem. 2008 73 427
    • (2008) J. Org. Chem. , vol.73 , pp. 427
    • Kyne, S.H.1    Schiesser, C.H.2    Matsubara, H.3
  • 27
    • 33947108931 scopus 로고    scopus 로고
    • One possibility is hydrogen abstraction from these radicals by tin radical and/or AIBN. For a role of AIBN in "oxidative hydrogen abstraction," see:
    • Y. Uenoyama T. Fukuyama I. Ryu Org. Lett. 2007 9 935
    • (2007) Org. Lett. , vol.9 , pp. 935
    • Uenoyama, Y.1    Fukuyama, T.2    Ryu, I.3
  • 32
    • 0028296779 scopus 로고
    • In previous work, BHandHLYP performs as well as higher correlation techniques such as CCSD(T) or QCISD for calculating radical processes. In addition, results generated using DZP proved to be very similar to those obtained using 6-311G** for reactions involving chlorine silicon and sulfur. See
    • S. -H. Chen S. Huang Q. Gao J. Golik V. Farina J. Org. Chem. 1994 59 1475
    • (1994) J. Org. Chem. , vol.59 , pp. 1475
    • Chen, S.-H.1    Huang, S.2    Gao, Q.3    Golik, J.4    Farina, V.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.