Abstract
IN a recent monograph1, C. C. Price refers to a publication by me2 in which reference was made to the formation of unsaturated alcohols of the general type CR2 : CR.CH2.CH2OH by the catalysed reaction3 of formaldehyde with the olefines CR2 : CR.CH3. Price states, "The reaction . . . has been interpreted as involving attack at the ‘‘active α-position of the double bond ; but it is very difficult to account for the catalytic effect of acids by such a mechanism. It seems much more likely that all the reactions involve a similar intermediate." This common intermediate is , formed by the addition of the formaldehyde cation to the olefinic bond. The formation of 3-methyl-δ3-butenl-ol from isobutylene is then formulated thus :
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References
"Reactions at Carbon-Carbon Double Bonds", 45 (Interscience Publishers, Inc., New York, 1946).
Baker, J. Chem. Soc., 296 (1944).
Brit. Pat. No. 545,191 (1942).
J. Franklin Inst., 226, 293 (1938).
Price, private communication.
Baker and Holdsworth, J. Chem. Soc., 724 (1945).
Baker and Nathan, J. Chem. Soc., 1844 (1935). Baker, J. Chem. Soc., 1150 (1939). Mulliken, Rieke and Brown, J. Amer. Chem. Soc., 63, 41 (1941)
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B., J. Olefine Reactions Catalysed by Lewis Acids. Nature 161, 171–172 (1948). https://doi.org/10.1038/161171a0
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DOI: https://doi.org/10.1038/161171a0
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