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Tris(pentafluorophenyl)borane is a key reagent leading to the concept of frustrated Lewis pairs. The combination of BCF and bulky basic phosphines, such as tricyclohexylphosphine (PCy 3) cleaves H 2: [11] (C 6 F 5) 3 B + PCy 3 + H 2 → (C 6 F 5) 3 BH − + HPCy 3 + Many related phosphines, boranes, and substrates participate in related reactions.
In this reaction, PCy 3 (the Lewis base) and B(C 6 F 5) 3 (the Lewis acid) cannot form an adduct due to the steric hindrance from the bulky cyclohexyl and pentafluorophenyl groups. The proton on the phosphorus and hydride from the borate are now ‘activated’ and can subsequently be ‘delivered’ to an organic substrate, resulting in ...
Boranes can be optimized to work on less activated substrates. Tris(pentafluorophenyl)borane [B(C 6 F 5) 3] is a strongly Lewis acidic borane which functions well in 1,1 carboborations with both activated and unactivated substrates, and it allows for the reaction to be facilitated with more mild conditions. [3]
2 Reactions. 3 Compounds. 4 References. Toggle the table of contents. Sulfinylamine. ... (pentafluorophenyl)borane, can attach to the NSO chain to yield a R' 3 P=N ...
The anion is tetrahedral with B-C bond lengths of approximately 1.65 Angstroms. The salt has only been obtained as the etherate, and the crystallography confirms that four ether (OEt 2) molecules are bound to the lithium cation, with Li-O bond lengths of approximately 1.95 Å.
Triphenylborane is made commercially by a process developed by Du Pont for use in its hydrocyanation of butadiene to adiponitrile, a nylon intermediate. Du Pont produces triphenylborane by reacting sodium metal, a haloaromatic (chlorobenzene), and a secondary alkyl borate ester.
Also called "banana borane", it exists as a dimer. It can be distilled without decomposition at 195 °C (12mm Hg). Reactions with 9-BBN typically occur at 60–80 °C, with most alkenes reacting within one hour. Tetrasubstituted alkenes add 9-BBN at elevated temperature. Hydroboration of alkenes with 9-BBN proceeds with excellent regioselectivity.
Tris(pentafluorophenyl)borane This page was last edited on 15 April 2024, at 06:55 (UTC). Text is available under the Creative Commons Attribution ...