Benzylidene acetals of the D-ribonolactones

A structural reassessment

Neil Baggett, J. Grant Buchanan, Moutie Y. Fatah, C. H. Lachut, Kevin J. McCullough, John M. Webber

Research output: Contribution to journalArticle

Abstract

The product of the reaction of D-ribono-1,4-lactone with benzaldehyde and concentrated HCl has been shown, by X-ray crystallography of its acetate, to be 3,4-O-(R)-benzylidene-D-ribono-1,5-lactone and not the 3,5-acetal as previously suggested; with ZnCl2 as catalyst the products are 2,3-O-(R)- and -(S)-benzylidene-D-ribono-1,4-lactone, the former preponderating.

Original languageEnglish
Pages (from-to)1826-1827
Number of pages2
JournalJournal of the Chemical Society, Chemical Communications
Issue number24
Publication statusPublished - 1985

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Acetals
X ray crystallography
Lactones
Acetates
Catalysts
D-ribono-1,4-lactone
ribonolactone
benzaldehyde

Cite this

Baggett, N., Buchanan, J. G., Fatah, M. Y., Lachut, C. H., McCullough, K. J., & Webber, J. M. (1985). Benzylidene acetals of the D-ribonolactones: A structural reassessment. Journal of the Chemical Society, Chemical Communications, (24), 1826-1827.
Baggett, Neil ; Buchanan, J. Grant ; Fatah, Moutie Y. ; Lachut, C. H. ; McCullough, Kevin J. ; Webber, John M. / Benzylidene acetals of the D-ribonolactones : A structural reassessment. In: Journal of the Chemical Society, Chemical Communications. 1985 ; No. 24. pp. 1826-1827.
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Baggett, N, Buchanan, JG, Fatah, MY, Lachut, CH, McCullough, KJ & Webber, JM 1985, 'Benzylidene acetals of the D-ribonolactones: A structural reassessment', Journal of the Chemical Society, Chemical Communications, no. 24, pp. 1826-1827.

Benzylidene acetals of the D-ribonolactones : A structural reassessment. / Baggett, Neil; Buchanan, J. Grant; Fatah, Moutie Y.; Lachut, C. H.; McCullough, Kevin J.; Webber, John M.

In: Journal of the Chemical Society, Chemical Communications, No. 24, 1985, p. 1826-1827.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Benzylidene acetals of the D-ribonolactones

T2 - A structural reassessment

AU - Baggett, Neil

AU - Buchanan, J. Grant

AU - Fatah, Moutie Y.

AU - Lachut, C. H.

AU - McCullough, Kevin J.

AU - Webber, John M.

PY - 1985

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AB - The product of the reaction of D-ribono-1,4-lactone with benzaldehyde and concentrated HCl has been shown, by X-ray crystallography of its acetate, to be 3,4-O-(R)-benzylidene-D-ribono-1,5-lactone and not the 3,5-acetal as previously suggested; with ZnCl2 as catalyst the products are 2,3-O-(R)- and -(S)-benzylidene-D-ribono-1,4-lactone, the former preponderating.

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JO - Journal of the Chemical Society, Chemical Communications

JF - Journal of the Chemical Society, Chemical Communications

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Baggett N, Buchanan JG, Fatah MY, Lachut CH, McCullough KJ, Webber JM. Benzylidene acetals of the D-ribonolactones: A structural reassessment. Journal of the Chemical Society, Chemical Communications. 1985;(24):1826-1827.