Interplay of theory and experiment: Reversal of the torquoselectivity of the electrocyclic ring opening of 3-acetylcyclobutene by a Lewis acid

Journal of Organic Chemistry

Volumn 61, Issue 2, 1996, Pages 640-646

  Niwayama, Satomi ^a,b  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0011749135     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951047j     Document Type: Article

References (34)

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31. During this period of reaction, remarkable reaction rate ac-celeration was not observed.
32. These product ratios were determined on the basis of the relative intensities of the singlet signals from the proton of acetyl groups of E-diene 20 and Z-diene 21 at regular time intervals. The plot of the ratios of 20 to 21 versus reaction time gave nearly flat lines for both uncatalyzed and catalyzed thermolyses during the initial stage of the ring openings. The kinetic ratios were determined by extrapolating these plots to time zero.
33. 25 However, this argument would require more systematic theoretical study.
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