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Generation of Simple Enols in Non-aqueous Solution by Fast Double-bond Migration of Allylic Alcohols with Rhodium(I) and Iridium(I) Complexes

DOI: 10.1039/DT9910000443

Source and publish data:

Journal of the Chemical Society, Dalton Transactions p. 443 - 448 (1991)

Update date:2022-07-30

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Authors:

Chin, Chong ShikChin, Chong Shik

Lee, ByeongnoLee, Byeongno

Kim, SangtaeKim, Sangtae

Chun, JongpilChun, Jongpil

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Article abstract of DOI:10.1039/DT9910000443

The complexes ClO4 1 and ClO4 2 (cod = cycloocta-1,5-diene), rapidly catalyse the double-bond migration of 2-ethylprop-2-en-1-ol 3 and prop-2-en-1-ol 4, respectively to generate a significant amount of the enols 2-methylbut-1-en-1-ol 5 and prop-1-en-1-ol 6 in the absence of a solvent and in CD3COCD3.Both enols 5 and 6 are quite stable and slowly undergo ketonization to the corresponding carbonyl compounds at room temperature in the absence of a solvent and in aprotic solvents.Detailed 1H NMR spectral data at 300 MHz suggest that two isomers (Z and E) of the compound 5 are simultaneously produced in the reaction of 3 and 1, the ratio of the isomers (major : minor) being ca. 6-9:1.Reaction of compound 4 with 2 also generates the Z (major) and E isomers (minor) of 6.The Z isomer initially generated rapidly undergoes isomerization to give the E isomer in the presence of 2, while both the Z and E isomers relatively slowly undergo ketonization.Additional 1H and 13C NMR and infrared spectral data for Me2C=CHOD and Me2CDCHO are reported with some experimental details.

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