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Additional info for Boronic Acids: Preparation and Applications in Organic Synthesis, Medicine and Materials (Volume 1 and 2), Second Edition
11) . , 29 versus 28). Presumably, the stabilizing effect of BÀO conjugation via overlap of boron with oxygen lone pairs is geometrically optimal in the larger rings. 9) represent a useful class of boronic acid derivatives . 11 Relative thermodynamic stability in a series of boronic esters. Other N-substituted derivatives were characterized . The presence of internal coordination between the nitrogen lone pair and borons vacant orbital constitutes a unique structural characteristic of these tetrahedral derivatives.
14). The existence of a seven-membered trans 1 : 2 adduct of a glucopyranoside was recently demonstrated by NMR spectroscopy . This behavior can be explained in terms of the large energy required for the trans-diol to adopt a coplanar orientation, which would increase ring strain and steric interactions between axial atoms. 15) . 11) . , 29 versus 28). Presumably, the stabilizing effect of BÀO conjugation via overlap of boron with oxygen lone pairs is geometrically optimal in the larger rings.
For example, a variety of simple alkylboronic acids were unaffected by prolonged heating in 40% aqueous HBr or HI . Like arylboronic acids, however, deboronation is observed in hot basic aqueous solutions . 5). 1). 3 Boronic Acid Derivatives For the sake of convenience in their puriﬁcation and characterization, boronic acids are often best handled as ester derivatives where the two hydroxyl groups are masked. On the other hand, transformation of the hydroxyl groups into other substituents such as halides or borate salts may also provide an increase in reactivity necessary for a number of synthetic applications.