Two novel routes to spiro[3.4]octan-1-ones

Smith, Amos B.; Foster, A. M.; Agosta, William C.

doi:10.1021/ja00769a062

Cited by 17 publications

(10 citation statements)

References 4 publications

(8 reference statements)

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“…Tremella mesenterica, NRRL Y-61587) are obtainable from the 13C nmr spectrum. Chemical evidence has indicated that the glucan contains two types of linkage, 1 4-a and 1 6-a, in an approximate ratio of 2:1.7 Thus, one might expect different 13C resonance frequencies for the various anomeric, four, and six carbon atoms, depending on whether or how they are linked. Examination of the (1) A. S. Perlin and B. Casu, Tetrahedron.…”

mentioning

confidence: 99%

Determination of the composition and sequence of a glucan containing mixed linkages by carbon-13 nuclear magnetic resonance

Jennings¹,

Smith²

1973

J. Am. Chem. Soc.

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mentioning

confidence: 99%

Determination of the composition and sequence of a glucan containing mixed linkages by carbon-13 nuclear magnetic resonance

Jennings¹,

Smith²

1973

J. Am. Chem. Soc.

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“…Similar reactions with α,β-unsaturated carbonyl compounds involving hydrogen abstraction and radical combination have been previously reported, often without considering them in a broader context of organic synthesis [79,80,[101][102][103][104][105][106][107][108][109][110][111][112][113]. Acetone is frequently used as a sensitizer in photochemical reactions of α,β-unsaturated lactones.…”

Section: Intramolecular Radical Addition With Electronically Excited mentioning

confidence: 63%

Photochemically induced radical reactions with furanones

Oelgemöller

Hoffmann

2015

Pure and Applied Chemistry

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Radicals are easily generated via hydrogen transfer form secondary alcohols or tertiary amines using photochemical sensitization with ketones. They can subsequently add to the electron deficient double bond of furanones. The addition of the alcohols is particularly efficient. Therefore, this reaction was used to characterize and to compare the efficiency of different photochemical continuous flow microreactors. A range of micro-structured reactors were tested and their performances evaluated. The enclosed microchip enabled high space-time-yields but its microscopic dimensions limited its productivity. In contrast, the open microcapillary model showed a greater potential for scale-up and reactor optimization. A 10-microcapillary reactor was therefore constructed and utilized for typical R&D applications. Compared to the corresponding batch processes, the microreactor systems gave faster conversions, improved product qualities and higher yields. Similar reactions have also been carried out with electronically excited furanones and other α,β-unsaturated ketones. In this case, hydrogen is transferred directly to the excited olefin. This reaction part may occur either in one step, i.e., electron and proton are transferred simultaneously, or it may occur in two steps, i.e., the electron is transferred first and the proton follows. In the first case, a C-C bond is formed in the α position of the α,β-unsaturated carbonyl compound and in the second case this bond is formed in the β position. For the first reaction, the influence of stereochemical elements of the substrate on the regioselectivity of the hydrogen abstraction on the side chain has been studied.

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“…The migration of alkoxy groups in molecular rearrangements is not common, and alkoxy migration from carbon to nitrogen is rare. 1 We now report such a rearrangement. (1) Alkoxy groups migrate to a minor extent in the decomposition of certain alkoxycarbonylnitrene precursors, giving alkoxyisocya-…”

Section: Gp-17319mentioning

confidence: 68%

“…1 We now report such a rearrangement. (1) Alkoxy groups migrate to a minor extent in the decomposition of certain alkoxycarbonylnitrene precursors, giving alkoxyisocya-…”

Section: Gp-17319mentioning

confidence: 68%

“…Finally a brief comment concerning the cyclopropanes should be made. The yields are too low to permit rigorous conclusions, but there is clearly greater loss of stereochemistry in the trans (1) series than in the isomeric cis (2) series. This is reminiscent of the unexplained observation that gas-phase pyrolysis of both cis-and fra«5-2,3-dimethylcyclobutanone yields 1,2dimethylcyclopropane chiefly as the cis isomer.…”

mentioning

confidence: 96%

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