2000
DOI: 10.1021/jo991803b
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Abstract: Bicyclic cyclopropenes 14a, 14b, and 26 were prepared by various synthetic routes. Polymer rose Bengal (p-RB) photosensitized oxygenation of bicyclooctenes 14a,b in CDCl(3) proceeded sluggishly (variable O(2) uptake of ca. 0.35-0.75 equiv in 8 h) and was accompanied by sensitizer bleaching. Preparative gas chromatography of the complex product mixtures from 14a and 14b yielded both dienes (Z- and E-29, 30, and 31) and enones (E- and Z-12, 32, 34). By contrast, p-RB photosensitized oxidation of bicyclononene 26… Show more

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Cited by 16 publications
(6 citation statements)
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“…Dussault found evidence for this step to be a sequential singlet oxygenation of the enol double bond of the 1,3-diene tautomer to give a 2-hydroperoxy-3-enone followed by a peroxyl radical rearrangement, proceeding also in the dark and amenable to acceleration by radical sources such as AIBN or TBHP. Frimer et al reported a similar domino two-step process for the conversion of 2-exo-alkylidenecycloalkanones to mixtures of hemiketal endoperoxides and allylic hydroperoxides which can be inhibited with DABCO and with radical scavengers such as DTBP …”
mentioning
confidence: 99%
“…Dussault found evidence for this step to be a sequential singlet oxygenation of the enol double bond of the 1,3-diene tautomer to give a 2-hydroperoxy-3-enone followed by a peroxyl radical rearrangement, proceeding also in the dark and amenable to acceleration by radical sources such as AIBN or TBHP. Frimer et al reported a similar domino two-step process for the conversion of 2-exo-alkylidenecycloalkanones to mixtures of hemiketal endoperoxides and allylic hydroperoxides which can be inhibited with DABCO and with radical scavengers such as DTBP …”
mentioning
confidence: 99%
“…Optical rotations were measured with a JASCO DIP-370 polarimeter. All enol silyl ethers prepared in this study are known compounds: 11, 24 12, 25 13, 25 14, 26…”
Section: Discussionmentioning
confidence: 99%
“…In the majority of homolytic reactions the carbonoxygen bond suffered the rupture [124]. The reduction, in particular, of epoxides 142 and 143 was among first instances of application of tributyltin hydride [125,126] (Scheme 69).…”
Section: Methods and Mechanisms Of Epoxy Compounds Reductionmentioning
confidence: 99%