메뉴 건너뛰기




Volumn 68, Issue 26, 2003, Pages 10175-10177

Reaction of Alkynes with Iodine Monochloride Revisited

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; IODINE COMPOUNDS; REACTION KINETICS; STEREOCHEMISTRY;

EID: 0346992392     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035372f     Document Type: Article
Times cited : (50)

References (32)
  • 16
    • 0347691529 scopus 로고    scopus 로고
    • note
    • The reaction between 1 and 5-substituted (Z)-2-methyl-2-en-4-ynoic acids provides a mixture of 6-substituted 5-iodo-3-methyl-2H-pyran-2-ones and (E)-3-methyl-5-ylidene-5H-furan-2-ones in which these last compounds are the minor components (see: ref 10).
  • 18
    • 0345799523 scopus 로고    scopus 로고
    • note
    • 13C HMBC (heteronuclear multiple-bond correlation).
  • 19
    • 0345799524 scopus 로고    scopus 로고
    • note
    • GLC analysis showed that (E)-5a was contaminated by less than 10% of (Z)-5a.
  • 21
    • 0347691527 scopus 로고    scopus 로고
    • Reference 1, p 278
    • Reference 1, p 278.
  • 22
    • 37049126017 scopus 로고
    • This assignment supports the formation of a cyclic iodonium intermediate similar to that previously proposed for the electrophilic addition of I-X species to dialkyl acetylenes [Bassi, P.; Tonellato, U. J. Chem. Soc., Perkin Trans. 2 1973, 669].
    • (1973) J. Chem. Soc., Perkin Trans. 2 , pp. 669
    • Bassi, P.1    Tonellato, U.2
  • 23
    • 0346430625 scopus 로고    scopus 로고
    • note
    • The regiochemistry of 6, which was assigned on the basis of a principle similar to that used to establish the structures of 5a-d, proved to be in agreement with that of the products of the reaction of 1 either with alkylethynes in acetonitrile (see ref 4) or with ethyl 3-butynoate in CC14, AcOEt, AcOH, or EtCOOH solution (see ref 3).
  • 24
    • 0346430623 scopus 로고    scopus 로고
    • note
    • We used MOPAC 97 software for Chem3D v. 5 (MNDO method) by Cambridgesoft.
  • 30
    • 84985527614 scopus 로고
    • The chemical shifts of acetylenic carbon atoms have already been used as an appoximative measure of the zonal charge density [Meier, H.; Stavidrou, E.; Storek, C. Angew. Chem., Int. Ed. Engl. 1986, 25, 809. Rosenberg, D.; Drenth, W. Tetrahedron 1971, 27, 3893].
    • (1986) Angew. Chem., Int. Ed. Engl. , vol.25 , pp. 809
    • Meier, H.1    Stavidrou, E.2    Storek, C.3
  • 31
    • 0004928343 scopus 로고
    • The chemical shifts of acetylenic carbon atoms have already been used as an appoximative measure of the zonal charge density [Meier, H.; Stavidrou, E.; Storek, C. Angew. Chem., Int. Ed. Engl. 1986, 25, 809. Rosenberg, D.; Drenth, W. Tetrahedron 1971, 27, 3893].
    • (1971) Tetrahedron , vol.27 , pp. 3893
    • Rosenberg, D.1    Drenth, W.2
  • 32
    • 0347060824 scopus 로고    scopus 로고
    • note
    • Two tables containing either the chemical shift values of the acetylenic carbon atoms of compounds 2, 3, and 4 or the resulting chemical shift differences Δδ are reported in the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.