Potassium triphosphate is a surprisingly active catalyst for the catalytic transfer hydrogenation of carbonyl compounds. A pretreatment at 600 °C is critical to obtain the active material. Temperature programmed desorption of CO2 indicates that sites of lower basicity were created after heat treatment for 5 h as compared to 1 h. With 2-propanol as hydride source, aromatic aldehydes were reduced to the corresponding alcohols with high rates. The presence of electron withdrawing chloro- and nitro-substituents at the benzene ring increases the rate of reaction compared with unsubstituted benzaldehyde, while electron donating methyl or 2-propyl groups has the opposite effect. Ketones were reduced with a lower rate of reaction than aldehydes. The role of K3PO4 as a heterogeneous catalyst is indicated by a complete lack of reaction in the absence of the solid base and by studies with competing substrates. The latter studies suggest that the catalytic transfer hydrogenation of benzaldehyde and chlorinated benzaldehydes takes place at different surface sites.
ChemInform Abstract Methoxycarbonylsulfamoyl chloride (III), prepared from chlorosulfonyl isocyanate (I), is converted to the inner salt (V) which reacts with the α-stannyl alcohols, generated from the ketones (VI) and tributylstannylmagnesium chloride (VII), to produce the intermediate stannyl sulfamates (VIII). These decompose upon heating to yield the vinylstannanes (IX). Butanone (X) is transformed into the isomeric alkenyltin compounds (XI) and (XII) by this method.
Tributylstannyl isocyanate (III) which is prepared from the inner salt (I) and tributylstannane (II) as mentioned in the title is observed as a by‐product in the formation of vinylic stannanes, e.g. (V), by dehydration of 1‐stannylcycloalkanols such as (IV) with the reagent (I).
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