Allyl Alkyl Carbonates

Dedicated to my family

Introduction

Allyl methyl carbonate is the simplest allyl alkyl carbonate. It was first synthesised by Hermann Otto Laurenz Fischer in 1929.[1] In general, a synthesis of these carbonates is possible in high yields starting from allyl alcohols, which can be converted with dialkyl dicarbonates[2] or alkyl chloroformates[3] under basic conditions (e.g., BuLi, pyridine) into the corresponding allyl alkyl carbonates. Allyl carbonates are highly versatile reagents, and they can be used both for nucleo- and electrophilic reactions. Furthermore, the introduction of allyl groups is of high synthetic value, because they can be easily transformed into other functional groups. Traditional allylation reagents, like allyl bromide, require the addition of a base. An advantage of allyl alkyl carbonates is that no additional base is needed because of the cleavage of the alkyl carbonate moiety into carbon dioxide and an alkoxide. This is the reason for the influence of the alkyl substituent (Me, t-Bu) on the reaction.

• References

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