Indirect cation pool method. Rapid generation of alkoxycarbenium ion pools from thioacetals

Journal of the American Chemical Society

Volumn 128, Issue 24, 2006, Pages 7710-7711

  Suga, Seiji ^a   Matsumoto, Kouichi ^a   Ueoka, Koji ^a   Yoshida, Jun Ichi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; CARBENOID; OXYCARBENIUM DERIVATIVE; THIOACETAL DERIVATIVE; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; CATION TRANSPORT; ELECTROCHEMICAL ANALYSIS; GLYCOSYLATION; INDIRECT CATION POOL METHOD; LOW TEMPERATURE PROCEDURES; MOLECULAR STABILITY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION KINETICS;

EID: 33745402910     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0625778     Document Type: Article

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40. 1H NMR, indicating that the equilibrium lay so far to 1, and the concentration of 2 was extremely small with such acids.
41. The reaction of 2 with 2 equiv of allyltrimethylsilane at -78 °C for 1 min followed by the treatment with 1-(trimethylsilyloxy)cyclohexene (2 equiv) at -78 °C for 10 min gave 3 in 81% yield. Only a trace amount of the product derived from 1-(trimethylsiloxy)cyclohexene was obtained, indicating that the reaction of 2 with allyltrimethylsilane was complete within 1 min at -78 °C.
42. - was added 1 (0.20 mmol), and the mixture was stirred for 5 min at -78 °C. Allyltrimethylsilane (0.50 mmol) was added, and the resulting solution was stirred at -78 °C for 15 min to obtain 3.