Efficient Isomerization of α-Pinene Oxide to Campholenic Aldehyde Promoted by a Mixed-Ring Analogue of Molybdenocene

Sofia M Bruno,Martyn Pillinger,Anabela A Valente,Isabel S Gonçalves,Carlos C Romão,Jeffrey Amelse

doi:10.1021/acssuschemeng.9b03087

Sofia M Bruno, Martyn Pillinger + Show 4 more

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https://doi.org/10.1021/acssuschemeng.9b03087

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Abstract

The MoIV complex [(η5-indenyl)(η5-cyclopentadienyl)Mo(MeCN)2](BF4)2 (1) has been used to promote two acid-catalyzed epoxide ring-opening reactions under ambient conditions. The alcoholysis of styre...

Highlights

Epoxides are important building blocks in organic synthesis owing to their ability to undergo various types of ring-opening reactions.[1,2,3,4] For these processes to be of practical use, mild reaction conditions are desirable and the selectivity towards the target product must be high.These requirements usually demand the use of an acid or base catalyst
The ability of 1 to promote acid-catalyzed reactions was first assessed by using the formation of EPE from styrene oxide (StyOx) as a model reaction (Scheme 1)
StyOx, we further explored the performance of 1 for the isomerization of PinOx to CPA using this ionic liquid (IL) and others as solvents (Table 2)

Summary

Introduction

Epoxides are important building blocks in organic synthesis owing to their ability to undergo various types of ring-opening reactions.[1,2,3,4] For these processes to be of practical use, mild reaction conditions are desirable and the selectivity towards the target product must be high.These requirements usually demand the use of an acid or base catalyst. The catalytic performance of 1 was further explored for the isomerization of PinOx to CPA in 1,2-dichloroethane (Table S1 in the Supporting Information).

Results

Conclusion