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A convenient preparative method of unsymmetrical ketones and aliphatic aldehydes by thermolysis of homoallylic alcohols
Author(s) -
Inaba Teruhiko,
Sakamoto Masami,
Watanabe Shoji,
Takahashi Ikufumi,
Fujita Tsutomu
Publication year - 1990
Publication title -
journal of chemical technology and biotechnology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.64
H-Index - 117
eISSN - 1097-4660
pISSN - 0268-2575
DOI - 10.1002/jctb.280480409
Subject(s) - yield (engineering) , thermal decomposition , chemistry , iodide , decomposition , organic chemistry , grignard reaction , reaction conditions , medicinal chemistry , catalysis , materials science , reagent , metallurgy
The thermolyses of various homoallylic alcohols, which are prepared from 1‐alken‐4‐ones (B) by Grignard reaction or reduction, afforded unsymmetrical ketones or aliphatic aldehydes in good yields. For example, the reaction of methylmagnesium iodide with 1‐nonen‐4‐one (1) gave 4‐methyl‐1‐nonen‐4‐ol (2) in 87% yield. The thermolysis of (2) at the temperature of 753 K gave 2‐heptanone (3) in 92% yield. By use of this method, we obtained a variety of 1‐alken‐5‐ones (J) which can be used as important intermediates of the preparation for dihydrojasmone or cis ‐jasmone.