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New preparative routes to cyclic peroxides and alkyl hydroperoxides

Korkodilos, Despina; (1993) New preparative routes to cyclic peroxides and alkyl hydroperoxides. Doctoral thesis (Ph.D), UCL (University College London). Green open access

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Abstract

To see if the peroxymercuration - demercuration reaction of cyclopropanes could be extended to include the intramolecular reaction, a series of aldehydes, RCHO (R=Me, Et,iPr, and c-C6H11) were converted via alkylation, cyclopropanation, oxidation, condensation with p-tosylhydrazine, reduction and perhydrolysis in to 2-hydroperoxyalkyl cyclopropanes and hence by cycloperoxymer- curation and reductive demercuration into the corresponding 3-alkyl-5-ethyl-1,2-dioxolanes. The preparation of 1-hydroperoxyalkyl- cyclopropanes was hampered by serious side reactions. In a separate study alkyl hydroperoxides R1R2C(OOH)CH2R3 were prepared from 30% H2O2 by hydroperoxymercuration of the corresponding alkenes R1R2C=CHR3 followed by addition to 2-methoxypropene, reductive demercuration with basic NaBH4 and deprotection of the resultant 2-methoxypropyl derivatives R1R2C(OO(CH2)2OMe)CH2R3 with aqueous acetic acid.

Type: Thesis (Doctoral)
Qualification: Ph.D
Title: New preparative routes to cyclic peroxides and alkyl hydroperoxides
Open access status: An open access version is available from UCL Discovery
Language: English
Additional information: Thesis digitised by ProQuest.
Keywords: Pure sciences; Peroxides
URI: https://discovery.ucl.ac.uk/id/eprint/10104174
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