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Volumn 62, Issue 6, 2006, Pages 1239-1244

Selective cleavage of acetals with ZnBr2 in dichloromethane

Author keywords

Acetals; Lewis acid; Mild conditions; Protecting groups; Selective cleavage

Indexed keywords

ACETAL DERIVATIVE; ALKENE DERIVATIVE; BENZENE DERIVATIVE; BROMINE DERIVATIVE; DICHLOROMETHANE; ZINC DERIVATIVE;

EID: 29744458182     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.10.064     Document Type: Article
Times cited : (12)

References (31)
  • 14
    • 0009933851 scopus 로고    scopus 로고
    • 2 was used to perform a double deprotection in substrates containing MEM, SEM or MOM groups in a 1,3-relationship to a dithiane unit: A. Vakalopoulos, and H.M.R. Hoffmann Org. Lett. 3 2001 2185 2188
    • (2001) Org. Lett. , vol.3 , pp. 2185-2188
    • Vakalopoulos, A.1    Hoffmann, H.M.R.2
  • 20
    • 29744448186 scopus 로고    scopus 로고
    • note
    • In relation to the mechanism of the reaction, one referee suggested one possible pathway in which a gem-dibromo derivative would be generated via intermediate A under the anhydrous conditions of the process: In control experiments with cyclohexanone acetals, we were not able to detect the formation of 1,1-dibromocyclohexane. In fact, we did isolate cyclohexanone, but it seems unlikely that it was formed through hydrolysis of the gem-dibromo derivative during the work-up. However, the formation of A does seem likely. Its hydrolysis to diol and ketone should occur easily during the work-up.
  • 27
    • 29744446713 scopus 로고    scopus 로고
    • note
    • (a) (P=TPS, TBS): see Ref. 13a.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.