Exhaustive C-methylation of carboxylic acids by trimethylaluminium: A new route to t-butyl compounds
Keyword(s):
Carboxylic acids are exhaustively C-methylated to t-butyl compounds by excess trimethylaluminium at c. 120�. Benzoic acid for example, gives t-butylbenzene. Similarly methylated are o-fluoro-, o-bromo-, and m-chloro-benzoic acids, 5-chloro-3-phenylsalicylic acid, 1-naphthoic acid, palmitic, oleic and undec-10-enoic acids. Adamantane-1-carboxylic acid gives mostly l-isopropenyladaman- tane, along with some 1-t-butyladamantane. Cinnamic acid gives mainly the allylically rearranged 2-methyl-4-phenylpent-2-ene. Triphenylacetic acid behaves atypically; 1,1,1-triphenylpropan-2-one and 3,3,3-triphenylpropyne result.
2000 ◽
Vol 38
(4)
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pp. 781-784
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2012 ◽
pp. 129-155
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2018 ◽
Vol 21
(4)
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pp. 298-301
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1989 ◽
Vol 54
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pp. 1219-1226
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