Beilstein J. Org. Chem.2016,12, 2668–2672, doi:10.3762/bjoc.12.263
SPB, whereas sugar alcohols of a larger carbon number were formed preferably in the presence of pVPB/NaSS.
Keywords: boronic acid compounds; formosereaction; sodium phenylboronate; sodium 4-vinylphenylboronate/sodium 4-styrenesulfonate copolymer; sugar alcohols; sugars; Findings
When an aqueous
solution of formaldehyde is warmed in the presence of a basic catalyst, a mixture of sugars and sugar alcohols, i.e., ‘formose’, is obtained. This reaction is called ‘formosereaction’ and was first reported by Butlerow, a Russian chemist, in 1861 [1]. Studies on formose reactions have revealed that the
formosereaction consists of several elemental reaction steps, e.g., acyloin condensation, aldol reaction, retro-aldol reaction, aldose–ketose isomerization, and Cannizzaro reaction, and the product, formose, is a complicated mixture of more than thirty species of sugars and sugar alcohols including non
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Graphical Abstract
Scheme 1:
Structures of the boronic acid compounds used in this study (i.e., SPB and pVPB/NaSS).
Beilstein J. Org. Chem.2016,12, 2663–2667, doi:10.3762/bjoc.12.262
Makoto Masaoka Tomohiro Michitaka Akihito Hashidzume Department of Macromolecular Science, Graduate School of Science, Osaka University, 1-1 Machikaneyama-cho, Toyonaka, Osaka 560-0043, Japan 10.3762/bjoc.12.262 Abstract The formosereaction in reverse micelles of aerosol-OT (AOT), triton X-100
(TX), and hexadecyltrimethylammonium bromide (CTAB) was investigated. Time–conversion data have indicated that the interfacial water layer of AOT reverse micelles is a medium that accelerates formation of glycolaldehyde in the formosereaction. The 13C NMR spectra for the products of the formose
reaction using formaldehyde-13C as starting material are indicative of the formation of ethylene glycol as a major product.
Keywords: aerosol-OT; formosereaction; hexadecyltrimethylammonium bromide; interfacial layer; reverse micelles; triton X-100; water pool; Findings
The ‘formosereaction’ yields a