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The McMurry reaction of benzophenone. The McMurry reaction is an organic reaction in which two ketone or aldehyde groups are coupled to form an alkene using a titanium chloride compound such as titanium(III) chloride and a reducing agent. The reaction is named after its co-discoverer, John E. McMurry.
Bis(pinacolato)diboron is a covalent compound containing two boron atoms and two pinacolato ligands. It has the formula [(CH 3) 4 C 2 O 2 B] 2; the pinacol groups are sometimes abbreviated as "pin", so the structure is sometimes represented as B 2 pin 2. It is a colourless solid that is soluble in organic solvents.
Pinacol is a branched alcohol which finds use in organic syntheses. It is a diol that has hydroxyl groups on vicinal carbon atoms. A white solid that melts just above room temperature, pinacol is notable for undergoing the pinacol rearrangement in the presence of acid and for being the namesake of the pinacol coupling reaction .
Pinacolone (3,3-dimethyl-2-butanone) is an important ketone in organic chemistry.It is a colorless liquid with a slight peppermint or camphor odor. It is a precursor to triazolylpinacolone in the synthesis of the fungicide triadimefon and in synthesis of the herbicide metribuzin.
The pinacol coupling can be followed up by a pinacol rearrangement. A related reaction is the McMurry reaction , which uses titanium(III) chloride or titanium(IV) chloride in conjunction with a reducing agent for the formation of the metal-diol complex, and which takes place with an additional deoxygenation reaction step in order to provide an ...
Migratory aptitude is the relative ability of a migrating group to migrate in a rearrangement reaction. [1] Migratory aptitudes vary in different reactions, depending on multiple factors. [2] In the Baeyer-Villiger reaction, the more substituted group, in general, migrates. [3]
The semipinacol rearrangement is a rearrangement reaction in organic chemistry involving a heterosubstituted alcohol of the type R 1 R 2 (HO)C–C(X)R 3 R 4. The hetero substituent can be a halogen (Cl, Br, I), a tosylate, a mesylate or a thiol group. This reaction proceeds by removal of the leaving group X forming a carbocation as electron ...
The A ring closure required two ketone groups for a pinacol coupling which were realized by oxidation of the C11 alcohol (TPAP, NMO) to ketone 36 and Wacker oxidation of the allyl group to diketone 37. After formation of the pinacol product 38 the benzyl groups (sodium, ammonia) and the trialkylsilyl groups (TBAF) were removed to form pentaol 39.