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Volumn 43, Issue 34, 2002, Pages 5985-5988

Determination of the extent to which an SE2′ reaction of a propargylsilane is anti

Author keywords

[No Author keywords available]

Indexed keywords

1,3 BISTRIMETHYLSILYLBUT 1 YNE; 2,4 DINITROBENZALDEHYDE; ALDEHYDE DERIVATIVE; BENZALDEHYDE DERIVATIVE; ISOBUTYRALDEHYDE; SILANE DERIVATIVE; TITANIUM TETRACHLORIDE; UNCLASSIFIED DRUG;

EID: 0037136131     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01250-9     Document Type: Article
Times cited : (5)

References (32)
  • 24
    • 0009907614 scopus 로고    scopus 로고
    • 5 unit derived from the propargylsilane. They were probably the result of electrophilic attack by a second adamantyl cation on the first-formed allene, but we were unable to stop the reaction at the earlier stage.
  • 26
    • 0009932273 scopus 로고    scopus 로고
    • Adamantyl cations, aldehydes and their acetals.
  • 27
    • 0009956429 scopus 로고    scopus 로고
    • Phenyldimethylsilyl in place of trimethylsilyl, and/or a terminal acetylene in place of the methyl-substituted 5.
  • 31
    • 0009931065 scopus 로고    scopus 로고
    • Neither we nor he has been able to prepare a crystalline derivative. Our choice of 2,4-dinitrobenzaldehyde was made in the forlorn hope that one of the products might crystallise.
  • 32
    • 0009953842 scopus 로고    scopus 로고
    • We have too little information to explain why isobutyraldehyde should be less selective than 2,4-dinitrobenzaldehyde. The reactive species will be the aldehyde coordinated to the Lewis acid. 2,4-Dinitrobenzaldehyde may be more reactive than isobutyraldehyde, but its coordinated form will probably be present in lower concentration. As a result it is only possible to guess whether its greater selectivity is a violation of the reactivity-selectivity principle. Since we do not know whether the erosion of stereospecificity is caused by rotation in the intermediate cation or by the initial attack not being anti to the silyl group, we can only speculate. One possibility is that the intermediate cation in the isobutyraldehyde reaction might be a little more stable than that in the 2,4-dinitrobenzaldehyde reaction, and might therefore have lived long enough to lose its stereochemical information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.