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

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

School of Engineering & Physical Sciences

Research output: Contribution to journal › Article › peer-review

28 Citations (Scopus)

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 language	English
Pages (from-to)	1826-1827
Number of pages	2
Journal	Journal of the Chemical Society, Chemical Communications
Issue number	24
Publication status	Published - 1985

Cite this

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title = "Benzylidene acetals of the D-ribonolactones: A structural reassessment",

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.",

author = "Neil Baggett and Buchanan, \{J. Grant\} and Fatah, \{Moutie Y.\} and Lachut, \{C. H.\} and McCullough, \{Kevin J.\} and Webber, \{John M.\}",

year = "1985",

language = "English",

pages = "1826--1827",

journal = "Journal of the Chemical Society, Chemical Communications",

issn = "0022-4936",

publisher = "Chemical Society",

number = "24",

}

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

Y1 - 1985

N2 - 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.

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.

UR - https://www.scopus.com/pages/publications/12944311131

M3 - Article

SN - 0022-4936

SP - 1826

EP - 1827

JO - Journal of the Chemical Society, Chemical Communications

JF - Journal of the Chemical Society, Chemical Communications

IS - 24

ER -

Benzylidene acetals of the D-ribonolactones: A structural reassessment

Abstract

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