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

✍ Scribed by Charles W. Jefford; Danielle Jaggi; Shigeo Kohmoto; John Boukouvalas; Gérald Bernardinelli

Publisher
John Wiley and Sons
Year
1984
Tongue
German
Weight
430 KB
Volume
67
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Summary The reaction of 4,5‐dimethyl‐4‐hydroperoxy‐1(4__H__)‐nephthalenone (9) with acetaldehyde, pivalaldehyde, benzaldehyde, and p‐chlorobenzaldehyde in CH~2~Cl~2~ 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‐3__H__, 5__H__ ‐[1,2,4]trio‐xino[3,2‐e]pyrrole in 24 and 20% yield, respectively.

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