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The Buchner ring expansion is a two-step organic C-C bond forming reaction used to access 7-membered rings. The first step involves formation of a carbene from ethyl diazoacetate , which cyclopropanates an aromatic ring.
The Buchner ring expansion reaction also involves the formation of a stabilised carbene. Cyclopropanation is also stereospecific as the addition of carbene and carbenoids to alkenes is a form of a cheletropic reaction , with the addition taking place in a syn manner.
The strategy can start with a Simmons-Smith-like cyclopropanation of a cyclic alkene. [8] A related cyclopropane-based ring expansion is the Buchner ring expansion. The Buchner ring expansion is used to convert arenes to cycloheptatrienes. The Buchner ring expansion is encouraged to open to the desired product by placing electron withdrawing ...
Carbenes had first been postulated by Eduard Buchner in 1903 in cyclopropanation studies of ethyl diazoacetate with toluene. [29] In 1912 Hermann Staudinger [30] also converted alkenes to cyclopropanes with diazomethane and CH 2 as an intermediate. Doering in 1954 demonstrated their synthetic utility with dichlorocarbene. [31]
Structure of the platinacyclobutane PtC 3 H 6 (bipy) derived from activation of cyclopropane.. In organometallic chemistry, the activation of cyclopropanes by transition metals is a research theme with implications for organic synthesis and homogeneous catalysis. [1]
A second major route to cyclopropanes entails addition of methylene (or its substituted derivatives) to an alkene, a process called cyclopropanation. [3] Substituted cyclopropanes undergo the reactions associated with the cyclopropyl ring or the substituents. Vinylcyclopropanes are a special case as they undergo vinylcyclopropane rearrangement.
In the case of arenes, the cyclopropanation product undergoes further electrocyclic ring opening to give cycloheptatriene products (Buchner ring expansion). [2] Alkenes undergo both C=C methylenation and C–H methylenation insertion to give a mixture of cyclopropanation and homologation products.
The Buchner–Curtius–Schlotterbeck reaction is the reaction of aldehydes or ketones with aliphatic diazoalkanes to form homologated ketones. [1] It was first described by Eduard Buchner and Theodor Curtius in 1885 [ 2 ] and later by Fritz Schlotterbeck in 1907. [ 3 ]