2004
DOI: 10.1023/b:rucb.0000035657.58776.cc
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Synthesis of peroxide compounds by the BF3-catalyzed reaction of acetals and enol ethers with H2O2

Abstract: For Abstract see ChemInform Abstract in Full Text.

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Cited by 23 publications
(12 citation statements)
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“…[2,[5][6][7] Thus, the hitherto unkown ethane-1,1-dihydroperoxide (2 a) exhibits a signal at 107.9 ppm in the 13 C NMR spectrum and one typical hydroperoxide-H signal (intensity two protons) at 9.71 ppm in the 1 H NMR spectrum. In combination with the HR-ESI MS result, the structure of 2 a could be proven unambiguously.…”
mentioning
confidence: 99%
“…[2,[5][6][7] Thus, the hitherto unkown ethane-1,1-dihydroperoxide (2 a) exhibits a signal at 107.9 ppm in the 13 C NMR spectrum and one typical hydroperoxide-H signal (intensity two protons) at 9.71 ppm in the 1 H NMR spectrum. In combination with the HR-ESI MS result, the structure of 2 a could be proven unambiguously.…”
mentioning
confidence: 99%
“…Further, when the reaction mixture was left standing at room temperature for a few days, X‐ray quality single crystals appeared, the crystal structures of which correspond to 2‐hydroxy‐2′‐hydroperoxydiadamantyl peroxide 2 . Previous reports on the formation of dimeric dihydroperoxides employed the use of acetals or ketals with anhydrous H 2 O 2 . Hence, the identification of 2 from the reaction mixture of commercially available adamantanone and 30 % aqueous solution of H 2 O 2 was unexpected.…”
Section: Resultsmentioning
confidence: 99%
“…The starting 1,1 bis(hydroxyperoxy)cyclo hexane (3a) and 1,1 bis(hydroxyperoxy)cyclododecane (3c) were synthesized by condensation of the corresponding cycloalkanone ketals with H 2 O 2 according to a procedure described earlier. 10,11 gem Bis(hydroperoxides) 3b,d,e were prepared analogously. Homocoupling of gem bis(hydroperoxides) 3a,b in the pres ence of BF 3 •OEt 2 .…”
Section: Methodsmentioning
confidence: 99%