What does semipinacol rearrangement mean?

Definitions for semipinacol rearrangement
semip·ina·col re·arrange·ment

This dictionary definitions page includes all the possible meanings, example usage and translations of the word semipinacol rearrangement.

Wiktionary

  1. semipinacol rearrangementnoun

    A rearrangement involving a carbocation with a hydroxy group adjacent to the electron-deficient centre.

Wikidata

  1. Semipinacol rearrangement

    The semipinacol rearrangement is a rearrangement reaction in organic chemistry involving a heterosubstituted alcohol of the type R1R2C–CR3R4. The hetero substituent can be a halogen, a tosylate, a mesylate or a thioxy group. This reaction proceeds by removal of the leaving group X forming a carbocation as electron deficient center. One of the adjacent alkyl groups then migrates to the positive carbon in a 1,2-shift. Simultaneously with the shift, a pi bond forms from the oxygen to carbon, assisting in driving the migrating group off its position. The result is a ketone or aldehyde. In another definition all semipinacol rearrangements "share a common reactive species in which an electrophilic carbon center, including but not limited to carbocations, is vicinal to an oxygen-containing carbon and can drive the 1,2-migration of a C–C or C–H bond to terminate the process, generating a carbonyl group ". The rearrangement reaction can be classified into 4 types. Type 1 concerns all 2-heterosubstitted alcohols. Substrates in type 2 rearrangements are allyl alcohols. The carbocation is formed by electrophilic addition to the alkene group with electrophiles such as halonium ions, Brønsted acids and Lewis acids. In type 3 the substrates are epoxides, notably 2,3-epoxy-alcohols and type 4 concerns the reactions of alpha hydroxyketones and alpha hydroxy imines. Reactions of type 4 are also called acyloin rearrangements.

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Numerology

  1. Chaldean Numerology

    The numerical value of semipinacol rearrangement in Chaldean Numerology is: 4

  2. Pythagorean Numerology

    The numerical value of semipinacol rearrangement in Pythagorean Numerology is: 3

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"semipinacol rearrangement." Definitions.net. STANDS4 LLC, 2024. Web. 19 Mar. 2024. <https://www.definitions.net/definition/semipinacol+rearrangement>.

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