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Volumn , Issue 2, 2004, Pages 426-430

Ring-Expansion of MCPs in the Presence of DIAD or DEAD and Lewis Acids

Author keywords

Diethyl azodicarboxylate (DEAD); Diisopropyl azodicarboxylate (DIAD); Lewis acids; Ring expansion

Indexed keywords

CYCLOPROPANE DERIVATIVE; DEUTERIUM; DICARBOXYLIC ACID; DIETHYL DIAZODICARBOXYLATE; DIISOPROPYL AZODICARBOXYLATE; LEWIS ACID; METHYLENECYCLOPROPANE DERIVATIVE; UNCLASSIFIED DRUG; WATER;

EID: 0842349082     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200300515     Document Type: Article
Times cited : (42)

References (72)
  • 2
    • 0039354995 scopus 로고    scopus 로고
    • Carbocyclic Three-Membered Ring Compounds
    • (Ed.: A. de Meijere), Thieme, Stuttgart
    • [1b] Carbocyclic Three-Membered Ring Compounds, in: Houben-Weyl, Vol. E17 (Ed.: A. de Meijere), Thieme, Stuttgart, 1996.
    • (1996) Houben-Weyl , vol.E17
  • 20
    • 0002110351 scopus 로고    scopus 로고
    • [2p] The mechanisms of reactions of MCPs with unsaturated carbon bonds have been extensively studied; review: M. Lautens, W. Klute, W. Tam, Chem. Rev. 1996, 96, 49.
    • (1996) Chem. Rev. , vol.96 , pp. 49
    • Lautens, M.1    Klute, W.2    Tam, W.3
  • 21
    • 0000154977 scopus 로고
    • (Eds.: B. M. Trost, I. Fleming, L. A. Paquette), Pergamon Press, Oxford
    • [2q] T. Ohta, H. Takaya, in: Comprehensive Organic Chemistry, vol. 5 (Eds.: B. M. Trost, I. Fleming, L. A. Paquette), Pergamon Press, Oxford, 1991, pp. 1185-1205.
    • (1991) Comprehensive Organic Chemistry , vol.5 , pp. 1185-1205
    • Ohta, T.1    Takaya, H.2
  • 35
    • 0141628939 scopus 로고    scopus 로고
    • For some more papers related to the ring-opening of MCPs by transition metal catalysts, please see: [3g] M. Shi, Y. Chen, B. Xu, Org. Lett. 2003, 5, 1225.
    • (2003) Org. Lett. , vol.5 , pp. 1225
    • Shi, M.1    Chen, Y.2    Xu, B.3
  • 53
    • 0001024887 scopus 로고
    • A. de Meijere has previously reported cycloadditions onto a unique olefin bicyclopropylidene in which the cyclobutanone was formed in a reaction between bicyclopropylidene and 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD) in wet acetone: A. de Meijere, I. Erden, W. Weber, D. Kaufmann, J. Org. Chem. 1988, 53, 152. In our MCPs system, though, the reactions between MCPs and DIAD in wet acetonitrile do not take place in the absence of Lewis acid.
    • (1988) J. Org. Chem. , vol.53 , pp. 152
    • De Meijere, A.1    Erden, I.2    Weber, W.3    Kaufmann, D.4
  • 54
    • 0001646582 scopus 로고
    • Such cyclobutanones can be formed in the reactions between MCPs and peracetic acid or MCPBA. [5a] J. K. Crandall, W. W. Conover, J. Org. Chem. 1978, 43, 3533.
    • (1978) J. Org. Chem. , vol.43 , pp. 3533
    • Crandall, J.K.1    Conover, W.W.2
  • 65
    • 0842342499 scopus 로고    scopus 로고
    • note
    • 18O content in 2.
  • 66
    • 0842299454 scopus 로고    scopus 로고
    • note
    • 16O) during the reaction.
  • 67
    • 33947571437 scopus 로고
    • The lower yield in relation to that shown in Table 1, entry 4 may be caused by the primary or secondary isotope effect. [8a] K. B. Wiberg, Chem. Rev. 1955, 55, 713.
    • (1955) Chem. Rev. , vol.55 , pp. 713
    • Wiberg, K.B.1
  • 69
  • 71
    • 0842342500 scopus 로고    scopus 로고
    • note
    • Actually, in order to remove the effect of the quality of the solvent (MeCN), we carried out the reactions by use of distilled MeCN under ambient atmosphere for other MCPs 1. The results are summarized in Tables 3 - 5. As can be seen from these Tables, this interesting ring-expansion reaction is also reproducible for various MCPs 1.
  • 72
    • 0842277702 scopus 로고    scopus 로고
    • note
    • The formation of diethyl hydrazine-1,2-dicarboxylate was confirmed by GLC and GC-MS. Quantitative analysis has also been carried out (see Supporting Information).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.