Complete kinetic analysis of thermal stereomutations among the eight 2,3-dideuterio-2-(methoxymethyl)spiro[cyclopropane-1,1'-indenes]

Baldwin, John E.; Black, Kersey A.

doi:10.1021/ja00316a036

Cited by 15 publications

(2 citation statements)

References 7 publications

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“…Thermal reactions were also carried out at higher temperatures by heating 3b and 4b in sealed glass tubes at 180 ЊC. Analysis ( 1 H-NMR) of the crude product showed that although reactions occurred (see below), the furanones 6b-8b (18), 4a (37) 3a (5), 4a (31) 3b (12), 4b (21) 4c (32) 3d (18), 4d (26) 3e (13), 4e (17) 3f (10), 4f (32) 12a (84) 12a (85) 12b (15-60) b 12c (31) 12e (26) 12f (14) 9a (2), 10a (6) 5a (22), 6a (5), 8a (1), 9a a Used as supplied (Aldrich). b The yield is reduced significantly on chromatography.…”

Section: Resultsmentioning

confidence: 99%

The reactions of diazo compounds with lactones. Part 1. Cyclopropanespiro-β-lactones from diketene: synthesis and reactions

Murphy

O’Sullivan

Geraghty

2000

J. Chem. Soc., Perkin Trans. 1

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Section: Resultsmentioning

confidence: 99%

The reactions of diazo compounds with lactones. Part 1. Cyclopropanespiro-β-lactones from diketene: synthesis and reactions

Murphy

O’Sullivan

Geraghty

2000

J. Chem. Soc., Perkin Trans. 1

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“…Dideuteriodiimidelc has been used recently for the stereospecific deuterium labelling of substituted cyclopropane compounds. 6 The authors went to great lengths to exclude proton sources from all the reactants, and they achieved 96% incorporation of deuterium across the double bond. Tritiated diimide has previously been reported for labelling steroids,7a fatty acids ,7b and amino acids7c at specific radioactivities up to 0.037 GBq mmol-1 (cf.…”

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confidence: 99%

Tritiated diimide: a regio- and stereo-selective tritium-labelling reagent

Saljoughian¹,

Williams²,

Morimoto³

et al. 1993

J. Chem. Soc., Chem. Commun.

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We report the synthesis of high specific activity tritiated diimide as a valuable reagent for the addition of tritium across symmetrical multiple bonds, and illustrate its application by regiospecific tritiation of a series of substituted cinnamates and an alkenyl organophosphonate.We have synthesized and used tritiated diimide (HN=NT) at high specific radioactivity (A,). The reagent effected doublebond reductions in the presence of other functionalities, including nitro, bromo, azido, methoxy, ester and phosphonate groups. The ability to hydrogenate multiple bonds in the presence of these functional groups will permit much simpler chemistry in many tritium-labelling reactions, and will often allow the tritiation procedure to be the final synthetic step in the production of a labelled compound.t t A preliminary report was presented at the Fourth International Symposium on the Synthesis and Applications of

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Thermal Stereomutations of Cyclopropanes and Vinylcyclopropanes

Baldwin

2009

Patai's Chemistry of Functional Groups

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Introduction Historical Synopsis Experimental Studies Correlations of Reaction Rate Constants Theoretical Models and Calculational Results Disparate Kinetic Results Conclusions Acknowledgements

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Complete kinetic analysis of thermal stereomutations among the eight 2,3-dideuterio-2-(methoxymethyl)spiro[cyclopropane-1,1'-indenes]

Cited by 15 publications

References 7 publications

The reactions of diazo compounds with lactones. Part 1. Cyclopropanespiro-β-lactones from diketene: synthesis and reactions

The reactions of diazo compounds with lactones. Part 1. Cyclopropanespiro-β-lactones from diketene: synthesis and reactions

Tritiated diimide: a regio- and stereo-selective tritium-labelling reagent

Thermal Stereomutations of Cyclopropanes and Vinylcyclopropanes

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