What question did this study set out to answer?

Investigate the mechanism and products of an unanticipated addition reaction observed when 2,3:4,5-di-O-isopropylidene-d-ribose diethyl dithioacetal is exposed to mercuric oxide and mercuric chloride.

May 23, 2001The Journal of Organic Chemistry

Investigation of an Unexpected Addition Reaction That Occurs when 2,3:4,5-Di-O-isopropylidene- d -ribose Diethyl Dithioacetal Is Treated with Mercuric Oxide and Mercuric Chloride

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Authors

TSThota SambaiahAstraZeneca (United States)PFPhillip E. FanwickPurdue University West Lafayette MCMark CushmanPurdue University West Lafayette

Discussion

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Implication

Experimental study uncovers an unexpected addition reaction during mercuric treatment of protected d-ribose dithioacetal, indicating alternative mechanistic pathways in carbohydrate synthesis.

Key Points

Investigate the mechanism and products of an unanticipated addition reaction observed when 2,3:4,5-di-O-isopropylidene-d-ribose diethyl dithioacetal is exposed to mercuric oxide and mercuric chloride.
Treated 2,3:4,5-di-O-isopropylidene-d-ribose diethyl dithioacetal with mercuric oxide and mercuric chloride under deprotection conditions.
Isolated and structurally characterized the resulting reaction products using chemical and spectroscopic methods.
Exposure of the protected ribose diethyl dithioacetal to mercuric salts triggered an unexpected addition reaction rather than standard dithioacetal hydrolysis.
Product characterization revealed structural modifications indicating the participation of reactive intermediates divergent from classical unmasking of the aldehyde.

Cite This Study

Sambaiah et al. (2001) studied this question.

synapsesocial.com/papers/6aa4a2efd2779b1afb94e295 https://doi.org/10.1021/jo001782h

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May 23, 2001The Journal of Organic Chemistry

Investigation of an Unexpected Addition Reaction That Occurs when 2,3:4,5-Di-O-isopropylidene- d -ribose Diethyl Dithioacetal Is Treated with Mercuric Oxide and Mercuric Chloride

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Authors

TSThota SambaiahAstraZeneca (United States)PFPhillip E. FanwickPurdue University West Lafayette MCMark CushmanPurdue University West Lafayette

Discussion

Member takes

Implication

Experimental study uncovers an unexpected addition reaction during mercuric treatment of protected d-ribose dithioacetal, indicating alternative mechanistic pathways in carbohydrate synthesis.

Key Points

Investigate the mechanism and products of an unanticipated addition reaction observed when 2,3:4,5-di-O-isopropylidene-d-ribose diethyl dithioacetal is exposed to mercuric oxide and mercuric chloride.
Treated 2,3:4,5-di-O-isopropylidene-d-ribose diethyl dithioacetal with mercuric oxide and mercuric chloride under deprotection conditions.
Isolated and structurally characterized the resulting reaction products using chemical and spectroscopic methods.
Exposure of the protected ribose diethyl dithioacetal to mercuric salts triggered an unexpected addition reaction rather than standard dithioacetal hydrolysis.
Product characterization revealed structural modifications indicating the participation of reactive intermediates divergent from classical unmasking of the aldehyde.

Cite This Study

Sambaiah et al. (2001) studied this question.

synapsesocial.com/papers/6aa4a2efd2779b1afb94e295 https://doi.org/10.1021/jo001782h

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