메뉴 건너뛰기




Volumn 52, Issue 25, 2011, Pages 3219-3222

Ethyl-2-(2-chloroethyl)acrylate: A new very versatile α- cyclopropylester cation synthon. Efficient synthesis of cyclopropane ester derivatives by Michael addition-induced cyclization reaction

Author keywords

Cyclopropyl cation; Cyclopropane; Michael addition initiated ring closure reactions

Indexed keywords

ACRYLIC ACID DERIVATIVE; ALPHA CYCLOPROPYLESTER; CARBON; CATION; CYCLOPROPANE DERIVATIVE; CYCLOPROPANE ESTER; ESTER; ESTER DERIVATIVE; ESTER ENOLATE; ETHYL 2 (2 CHLOROETHYL)ACRYLATE; NITROGEN; NUCLEOPHILE; PHOSPHORUS; SULFUR; UNCLASSIFIED DRUG;

EID: 79956205964     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.04.046     Document Type: Article
Times cited : (10)

References (27)
  • 24
    • 33947464960 scopus 로고
    • α-Chloro acetates are known to produce cyclopropane derivatives by Michael addition on electron deficient olefins, as reported in the McCoy reaction In our case, the reaction of α-chloro acetates with 2 or 11 led to a mixture of products which were not characterized
    • α-Chloro acetates are known to produce cyclopropane derivatives by Michael addition on electron deficient olefins, as reported in the McCoy reaction; McCoy, L. L. J. Am. Chem. Soc. 1958, 80, 6568. In our case, the reaction of α-chloro acetates with 2 or 11 led to a mixture of products which were not characterized.
    • (1958) J. Am. Chem. Soc. , vol.80 , pp. 6568
    • McCoy, L.L.1
  • 25
    • 79956210615 scopus 로고    scopus 로고
    • note
    • In the case of methyl cyanoacetate as the nucleophile, the desired cyclopropane derivative is obtained along with side products which might result from proton exchange (Scheme 4, equation E). The intramolecular proton exchange through a six-membered ring between the negatively charged oxygen atom of the ester enolate and the hydrogen atom flanked by both electron withdrawing groups (cyano and ester) could be a competitive pathway depending on the acidity of this proton and the conformation adopted by the ester enolate.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.