메뉴 건너뛰기




Volumn 1, Issue 22, 2003, Pages 4047-4057

Intramolecular radical additions to pyridines

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; FREE RADICALS; MOLECULAR DYNAMICS; PH EFFECTS; SAMARIUM COMPOUNDS; SATURATION (MATERIALS COMPOSITION);

EID: 0344084101     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b309331j     Document Type: Article
Times cited : (51)

References (55)
  • 22
    • 0037156631 scopus 로고    scopus 로고
    • The precise mechanism through which a hydrogen atom is lost from intermediates such as 4 has been the subject of much speculation. For our favoured explanation see: D. C. Harrowven and B. J. Sutton and S. Coulton, Tetrahedron, 2002, 58, 3387.
    • (2002) Tetrahedron , vol.58 , pp. 3387
    • Harrowven, D.C.1    Sutton, B.J.2    Coulton, S.3
  • 23
    • 0344563357 scopus 로고    scopus 로고
    • note
    • 1H NMR spectrum, allowed us to establish the identity of products with due rigour through NOE and related 2D NMR techniques. In contemporaneous studies we have found that oxygen substituents on the donor aryl radical can influence the course of cyclisation reactions of this type. Indeed, they appear to accelerate cyclisation reactions relative to hydrogen atom abstraction from tributyltin hydride.
  • 24
    • 0345425543 scopus 로고    scopus 로고
    • note
    • Two practical considerations led us to employ aryl iodides rather than aryl bromides in the ortho- and ipso-cyclisation reactions described herein. Firstly, the dichotomy outlined in Scheme 3 showed that side reactions were more significant when aryl bromides were employed. Secondly, with aryl bromides it was often necessary to add substantial quantities of the initiator AIBN in order to bring about complete conversion (on occasions, greater than a full equivalent!). By contrast, with aryl iodides it was usually possible to bring about complete convesion using 5-20 mol% AIBN. The switch was made after the experiments described in Schemes 8-10 had been conducted.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.