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The Simmons–Smith reaction is an organic cheletropic reaction involving an organozinc carbenoid that reacts with an alkene (or alkyne) to form a cyclopropane. [ 1 ] [ 2 ] [ 3 ] It is named after Howard Ensign Simmons, Jr. and Ronald D. Smith .
In chemistry a carbenoid is a reactive intermediate that shares reaction characteristics with a carbene. [1] In the Simmons–Smith reaction the carbenoid intermediate is a zinc / iodine complex that takes the form of I-CH 2-Zn-I. This complex reacts with an alkene to form a cyclopropane just as a carbene would do.
Carbene intramolecular reaction Carbene intermolecular reaction The 1,2-rearrangement produced from intramolecular insertion into a bond adjacent to the carbene center is a nuisance in some reaction schemes, as it consumes the carbene to yield the same effect as a traditional elimination reaction . [ 16 ]
The most reactive metals, such as sodium, will react with cold water to produce hydrogen and the metal hydroxide: 2 Na (s) + 2 H 2 O (l) →2 NaOH (aq) + H 2 (g) Metals in the middle of the reactivity series, such as iron , will react with acids such as sulfuric acid (but not water at normal temperatures) to give hydrogen and a metal salt ...
In the Arndt–Eistert reaction, an α-diazoketone is induced to release N 2, resulting in a highly reactive sextet carbon center adjacent to the carbonyl. Such species convert by a Wolff rearrangement to give an ester in the presence of alcohols. When applied to cyclic α-diazoketones, ring contraction occurs.
A transition metal carbene complex is an organometallic compound featuring a divalent carbon ligand, itself also called a carbene. [1] Carbene complexes have been synthesized from most transition metals and f-block metals, [2] using many different synthetic routes such as nucleophilic addition and alpha-hydrogen abstraction. [1]
The carbene carbon of a Fischer carbene is electrophilic in nature. Thus, Fischer carbenes exhibit similar reactivity compared to carbonyl compounds . Many of the reactions can be understood by using the carboxylic equivalent structure such as transesterification , Michael addition , and aldol reaction .
The elementary reaction responsible for water quantification in the Karl Fischer titration is oxidation of sulfur dioxide (SO 2) with iodine: . H 2 O + SO 2 + I 2 → SO 3 + 2 HI. This elementary reaction consumes exactly one molar equivalent of water vs. iodine.