- New Methods of Formation of Meta-Substituted Aromatic Compounds
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The addition of organolithium reagents to the oxa tricyclic ketone 1 occurs stereospecifically to produce the corresponding tertiary carbinols 2a-d.When the alcohols 2a-d are treated with TiCl4, ring fragmentation and dehydration occur to produce good yields of 5,6-dihydrobenzaldehydes 3a-d.Oxidation of aldehydes 3a-d then leads to the corresponding meta-substituted benzaldehydes 4a-d.Alternatively, use of the Lewis acid Me2BBr did not stop at the dihydrobenzaldehyde stage.Tautomerization of the diene aldehydes 3a-d produced meta-substituted benzyl alcohols 7a-d or benzyl bromides 8a-d under prolonged reaction times.The addition of silica gel to the reactions accelerated the formation of the benzyl bromides.
- Adams, Julian,Belley, Michel
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p. 3878 - 3881
(2007/10/02)
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- Heterocyclic substituted benzyl alcohol, insecticidal ester derivatives, and intermediates
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Disclosed and exemplified are insecticidal and acaricidal optionally substituted furylbenzyl, thienylbenzyl, pyrazinylbenzyl, or pyridinzylbenzyl esters of the pyrethroid acids, novel pyrethroid alcohols and other intermediates, and compositions, a method of use and a process for preparation of the esters.
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