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Scientific article
English

A New Approach to 1,2,4-Trioxanes from Cyclic Allylic Hydroperoxides

Published inHelvetica chimica acta, vol. 67, no. 8, p. 2254-2260
Publication date1984-12-19
Abstract

The reaction of 4,5-dimethyl-4-hydroperoxy-1(4H)-nephthalenone (9) with acetaldehyde, pivalaldehyde, benzaldehyde, and p-chlorobenzaldehyde in CH2Cl2 in the presence of Amberlyst-15 as catalyst gave the corresponding cis-3-methyl, t -butyl, phenyl and p -chlorophenyl derivatives of 10,10b-dimethylnaphtono[2,1-e][1,2,4]trioxin-6(5)H-one in 80-95% yields. Acetone reacted similarly with 9 to give the 3,3′ -dimethyl derivative. Configurations of all trioxinones were assigned by comparison of their spectral properties with that of the p -chloro derivative whose structure was determined by X-ray. 2,5-Diphenyl-2-hydroperoxypyrrole was less efficient that 9, but it condensed with acetaldehyde and pivaladehyde under the same conditions giving the cis - 3-methyl and cis - 3-(t -butyl) derivatives of 6,7a-diphenyl-4a, 7a-dihydro-3H, 5H -[1,2,4]trio-xino[3,2-e]pyrrole in 24 and 20% yield, respectively.

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Citation (ISO format)
JEFFORD, Charles et al. A New Approach to 1,2,4-Trioxanes from Cyclic Allylic Hydroperoxides. In: Helvetica chimica acta, 1984, vol. 67, n° 8, p. 2254–2260. doi: 10.1002/hlca.19840670831
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ISSN of the journal0018-019X
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