17526-10-2

Upstream product

• 16872-09-6 1,2-dicarba-closo-dodecaborane⁽¹²⁾ 
• 100-39-0 benzyl bromide 
• 19610-34-5 (1'-hydroxymethyl)-1,2-dicarba-closo-dodecaborane 
• 71-43-2 benzene 
• 100-44-7 benzyl chloride 
• 7439-95-4 magnesium 
• 36534-59-5 1-CH₂F-1,2-C₂HB₁₀H₁₀ 
• 109-72-8 n-butyllithium 
• 7553-56-2 iodine 
• 108-88-3 toluene 

Downstream Products

• 65062-89-7 1,2-C₂B₁₀H₁₁-1-(CH₂C₆H₄-4'-COCH₃) 
• 145826-18-2 C₆H₅CH(COOH)C₂(B₁₀H₁₀)COOH 

Relevant academic research and scientific papers

Reaction of carboryne with alkylbenzenes

Carboryne (1,2-dehydro-o-carborane), in situ generated from the precursor 1-iodo-2-lithiocarborane, reacted with alkylbenzenes to give two regioisomers of the [4 + 2] cycloadducts as the major products in moderate to good yields, in which the steric factors play an important role in the regioselectivity. Minor products derived from benzylic C-H insertion reaction, annulation reaction, tandem [4 + 2] cycloaddition/homo Diels-Alder reaction, and tandem ene reaction/[2 + 2] cycloaddition were also isolated and characterized in the reaction of carboryne with toluene. The presence of AgF in the above reaction produced no notable changes in the product distributions and yields.

Microwave-assisted synthesis of tricarbonyl rhenacarboranes: Steric and electronic effects on the 1,2 → 1,7 carborane cage isomerization

A series of tricarbonyl rhenacarboranes {[M][Re(CO)3(RR′ C2B9H9)]} (M = Na, K) were synthesized in water using microwave radiation with reaction times of less than 15 min. The novel complexes were isolated in good yields (57-94%) as either 3,1,2-(R = H: R′ = CH2Pyr 6; R′ = CH2Cy, 20) or 2,1,8-(R = H: R′ = H, 4; R′ = CH2PyrMe 12; R′ = CH 2PyrH, 13; R′ = Pyr, 15; R′ = Ph, 17; R = R′ = Bn, 19) metallacarboranes and characterized by multinuclear (1H, 11B, 13C) and NOE NMR spectroscopy, IR spectroscopy, mass spectrometry, and X-ray crystallography in the case of compounds 12 and 13. Carborane cage isomerization from the original 1,2 configuration to the 1,7 orientation occurred in cases where significant steric crowding was present at the metal center. Incorporation of a methylene spacer between the carborane cage and the six-membered ring as in 7 and 20 decreased steric strain such that the 3,1,2 configuration was maintained. Conversion of the 3,1,2 complex 6 to the 2,1,8 isomers 12 and 13 takes place at room temperature upon methylation or protonation of the pyridyl ring, indicating that electronic effects also play a significant role in the isomerization process.