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Volumn 72, Issue 3, 2007, Pages 977-983

Single-isomer iodochlorination of alkynes and chlorination of alkenes using tetrabutylammonium iodide and dichloroethane

Author keywords

[No Author keywords available]

Indexed keywords

HALOGEN COMPOUNDS; IODINE COMPOUNDS; ISOMERS; OLEFINS; STEREOCHEMISTRY;

EID: 33846935979     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo062188w     Document Type: Article
Times cited : (48)

References (41)
  • 4
    • 0002672933 scopus 로고
    • S, Ed, Ellis Horwood Limited: Chichester
    • McCleland, C. W. Synthetic Reagents; Pizey, J. S.. Ed.; Ellis Horwood Limited: Chichester, 1983; Vol. 5, pp 85-164.
    • (1983) Synthetic Reagents; Pizey, J , vol.5 , pp. 85-164
    • McCleland, C.W.1
  • 27
    • 33846917070 scopus 로고    scopus 로고
    • The E-esters were briefly photolyzed to generate the corresponding Z-isomers, and then the esters were reduced with DIBAL, giving the corresponding alcohols. Consistent with the structural assignments shown, nOe enhancements were observed between the methyl and methylene of the Z-isomer whereas these interactions were lacking in the E-isomer. See ref 8 for details
    • The E-esters were briefly photolyzed to generate the corresponding Z-isomers, and then the esters were reduced with DIBAL, giving the corresponding alcohols. Consistent with the structural assignments shown, nOe enhancements were observed between the methyl and methylene of the Z-isomer whereas these interactions were lacking in the E-isomer. See ref 8 for details.
  • 28
    • 33846908211 scopus 로고    scopus 로고
    • Diiodinated products were also detected by mass spectroscopy
    • Diiodinated products were also detected by mass spectroscopy.
  • 29
    • 33846897921 scopus 로고    scopus 로고
    • A control reaction performed by refluxing allyloxybenzene in DCE gave no reaction. This illustrated that the tetrabutylammonium iodide was an essential component of this process
    • A control reaction performed by refluxing allyloxybenzene in DCE gave no reaction. This illustrated that the tetrabutylammonium iodide was an essential component of this process.
  • 30
    • 33846931706 scopus 로고    scopus 로고
    • Full reaction details are described in the Supporting Information
    • Full reaction details are described in the Supporting Information.
  • 31
    • 33846929071 scopus 로고    scopus 로고
    • 4NI (3 equiv) in DCE. The solution was heated at reflux until consumption of starting material was complete as indicated by TLC.
    • 4NI (3 equiv) in DCE. The solution was heated at reflux until consumption of starting material was complete as indicated by TLC.
  • 32
    • 33846931012 scopus 로고    scopus 로고
    • 4NI in refluxing DCE for 18 h returned the material in an unaltered ratio (95 %, 12:13, 2.8:1).
    • 4NI in refluxing DCE for 18 h returned the material in an unaltered ratio (95 %, 12:13, 2.8:1).
  • 33
    • 33846920732 scopus 로고    scopus 로고
    • Detailed descriptions of the preparation of compounds 9, 12, 20, and 23 are found in ref 8.
    • Detailed descriptions of the preparation of compounds 9, 12, 20, and 23 are found in ref 8.
  • 36
    • 33744537310 scopus 로고    scopus 로고
    • Alternative preparation from epoxides: (a) Iranpoor, N.; Firouzabadi, H.; Azadi, R.; Ebrahimzadeh, F. Can. J. Chem. 2006, 84, 69.
    • Alternative preparation from epoxides: (a) Iranpoor, N.; Firouzabadi, H.; Azadi, R.; Ebrahimzadeh, F. Can. J. Chem. 2006, 84, 69.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.