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Ketene can be formed with different heteroatom bonded to the sp carbon atom, such as O, S or Se, respectively named ketene, thioketene and selenoketene. Ethenone, the simplest ketene, has different experimental lengths for each of the double bonds; the C=O bond is 1,160Å and the C=C bond is 1,314Å.
When reacting with either ketene or dimethylketene, the formation of the β-lactone product was favored, as this cyclization occurs via an attack on the terminal ketene carbonyl. [16] Cycloaddition of dimethylmethyleneketene and ketene to form a β-lactone and a cyclic 1,3-diketone [16]
Ketene, monoalkylketenes, and dimethylketene are usually allowed to react at or below room temperature, whereas the higher molecular weight ketenes can be heated to temperatures above 100°. The ketene is usually used in excess when dimerization is a major side reaction.
Ethenone is the formal name for ketene, an organic compound with formula C 2 H 2 O or H 2 C=C=O. It is the simplest member of the ketene class. It is an important reagent for acetylations .
Left structure is ketene form while right structure is ynolate form. As shown in Figure 5, ketenyl anion has two major resonance structures: ketenyl form and ynolate form. Due to the resonance structures, alkali metal cations can be coordinated to either at central carbon atom or terminal oxygen atom depending on its electronic structure.
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The general structure of a ketene. R is any group. It was here that he discovered the ketenes, a family of molecules characterized by the general form depicted in Figure 1. [3] Ketenes would prove a synthetically important intermediate for the production of yet-to-be-discovered antibiotics such as penicillin and amoxicillin. [4]
The acid chloride then reacts with diazomethane (R 2 = H), or occasionally a diazoalkyl, via the Arndt-Eistert procedure, to generate an α-diazo ketone, which will undergo a metal-catalyzed or photolyzed Wolff rearrangement, to give a ketene. The ketene can be trapped with any weak acid, such as an alcohol or amine, to form the ester or amide.