7318-84-5

Usage

InChI:InChI=1/C8H20B2O/c1-5-9(6-2)11-10(7-3)8-4/h5-8H2,1-4H3

Upstream product

• 97-94-9 triethyl borane 
• 12081-54-8 tetraethyldiborane⁽⁶⁾ 
• 4559-70-0 Diphenylphosphine oxide 
• 791-28-6 Triphenylphosphine oxide 
• 92784-88-8 {(diphenylphosphinoyloxy)diethylborane}2 
• 22100-19-2 (1-pyrrolyl)diethylborane 
• 1310-73-2 sodium hydroxide 
• 99829-81-9 {(dichloroaluminooxy)diethylborane}2 
• 138517-94-9 potassium 2,2,3,4,5-pentaethyl-2,5-dihydro-1,2,5-oxadiboratolate 
• 593-81-7 trimethylamine hydrochloride 
• 159087-72-6 rac-9-{(dimethylamino)ethylboryloxy}-10-ethyl-10-(1-ethylethenyl)-9-borabicyclo{3.3.2}decane 
• 5518-25-2 Diethylborane 
• 108342-97-8 (diphenylphosphinooxy)diethylborane 

Downstream Products

• 14695-69-3 4,4,8,8-tetraethylpyrazabole 
• 120610-81-3 2,2,4,4-tetraethyl-6,8-diphenyl-3-oxonia-1-aza-5-azonia-2,4-diboratabicyclo{3.3.0}octa-5,7-diene 
• 120610-80-2 2,2,4,4-tetraethyl-6-methyl-8-phenyl-3-oxonia-1-aza-5-azonia-2,4-diboratabicyclo{3.3.0}octa-5,7-diene 
• 92810-17-8 (C₆H₁₁)2P(O)OB(C₂H₅)2 

Relevant academic research and scientific papers

Rearragement and Degradation of Bicyclic Amine-Tetraalkyldiboroxanes

The amine-tetraalkyldiboroxanes 1,4,7,7' = Et; 1b: R1,4,7 = Et, R7' = Ph; 1b': R4,7,7' = Et, R1 = Ph; 1c: R1,7,7' = Et, R4 = Ph> react on heating by EtBO elimination and allylborane rearrangement to yield the allyl-aminoboranes Me2NB(Et)CH2C(R4)=C(R7,7') 4,7,7' = Et, 2b/2b': R4 = Et, R7,7' = Et, Ph; 2c: R4 = Ph, R7,7' = Et>: On heating above 60 deg C the diastereomeric syn/anti-1d/1d' (1d: R1,7 =C8H14, R4,7' = Et; 1d': R1,7' = C8H14, R4,7 = Et) give the unsaturated rac-amino-trialkyldiboroxane (rac-3) (X-ray structure analysis) by intramolecular 1,2-deaminoboration. rac-3 is characterized by reaction with (Et2BH)2 and (Et2BD)2 with formation of the 1,2,6-oxadiborinane 5 by evolution of H2 or HD respectively.The intramolecular CH-borylation of rac-3 is compared with those of the thujopsen hydrocarbons I-III. - Key Words: Amine-Diboroxanes, bicyclic / 1,2-Deaminoboration, intramolecular / Deoxy boration / Allyl-aminoboranes, organosubstituted, rearrangement / C-Borylation

Substituted 2,5-Dihydro-1,2,5-oxoniadiboratoles, cis-1,2-Diborylalkenes, and 1,2,5-Oxadiborolanes - Preparation and Characterization

The potassium salts (A: R = R' = Et; B: R2 = C8H14, R' = Me; C: R2 = C8H14, R' = Et) react with various electrophiles (H+, R+, Me3E(IV)+) to form substituted 1,3,2-diboroxanes (1, iso8b) including 1,2,5-oxadiborolanes (2, 4, 6, 9, 10), dialkylvinylboranes (1'), 2,5-dihydro-1,2,5-oxoniadiboratoles (3, 5) and cis-1,2-diborylalkenes (7, 8).In particular, A-C react with HCl (as Me3NHCl/THF or HCl/Et2O) to give O2 (1a; R = Me; 1b: R = Et), R2BCR'= Et; 2b: R2 = R' = Et) and (2a: R,R' = Et; 2b: R2 = C8H14, R' = Me; 2c: R2 = C8H14, R'= Et).With MeI in THF the cyclic compounds (3a) or (4b/4'b: R = Me; 4c/4'c: R = Et) and with Et3O*BF4 in CH2Cl2 the heterocycle (5a) and cis-EtOB(C8H14)C(Et)=C(Et)BEt (5c) and/or (6b: R = Me; 6c: R = Et) are obtained.The reactions of A with ClEl(IV)Me3(El(IV) = Si, Ge, Sn) lead to cis-Et2BC(Et)=CB(Et)OEl(IV)Me3 (El = Si (7a), Ge (8a)) and to cyclic (9a).The salts B and C react with ClEl(IV)Me3 (El(IV) = Si, Ge) to form cis-C8H14BC(R)=C(Et)B(Et)OEl(IV)Me3 (El(IV) = Si: 7b: R = Me; 7c: R = Et; El(IV) = GE: 8b: R= Me, 8c: R = Et).On heating 8b isomerizes to cis-Me3GeC(Me)=C(Et)B(Et)OBC8H14 (iso8b).From B and C with ClSnMe3 the substituted 1,2,5-oxadiborolanes (10b/10'b: R = Me; 10c: R = Et) are obtained together with (C8H14B)2O.Key Words: 1,2,5-Oxoniadiboratoles, 1,5-dihydro-, organo-substituted / 1,2,5-Oxadiborolanes, organo-substituted / 1,3,2-Diboroxanes, substituted with unsaturated residues / Boryl-germyl exchange / cis-1,2-Diborylalkenes, organo-substituted

Reactions of Diphenylphosphane Oxide with Organodiboranes(6) - Structure of a Zwitterionic Compound

(C6H5)2POB(C2H5)2 (3'a), prepared from diphenylphosphane oxide (C6H5)2P(O)H (1) and activated triethylborane (2a*), reacts with tetraalkyldiboranes(6) (R2BH)2 to form the BH3-addition compounds (C6H5)2P(BH3)OBR2 , 2BR , and 3B .The reaction of bis(9-borabicyclononane) (4c)2 with 1 leads to (C6H5)2POBC8H14 (3'c) or 3'c-4a and (C6H5)2PH (7) or (C6H5)2PH-HBC8H14 (7-4c).The crystalline zwitterionic (C6H5)2P(H)OB3 (X-ray analysis) is isolated from the reaction of 1 with (4a)2.

Reactions of (Organo)phosphorus-Oxygen Compounds with Diorgano-hydro-boranes

Trialkyl phosphites P(OR)3 react with tetraalkyldiboranes(6) (R'2-BH)2 in a temperature-dependent manner between 20 and 130 deg C to form the trialkyl phosphite-boranes (RO)3P-BHR'2, (RO)3P-BH2R', and (RO)3P-BH3, which have various stabilities toward alcohols.With bis(9-borabicyclononane) (1c)2 the easily protolyzed addition compounds are obtained . - Diorgano phosphites (RO)2P(O)H , triorgano phosphates (RO)3PO , and the monosaccharide-diphenyl phosphates 4f, 4g, and 4h are reduced by (1a)2 or (1c)2 to give H2, PH3, and insoluble yellow phosphorus compounds, respectively.Phosphoric acid (4e), their derivatives OP(OBR2)3 , and phenylphosphonic acid C6H5P(O)(OH)2 (6) are not deoxygenated at 130 deg C by (1a)2 to (1c)2. - Diorganophosphoiic acids R2P(O)OH and phenylphosphinic acid C6H5(H)P(O)OH (5c) are reduced by (1a)2-(1c)2.Reaction of 5a with (1a)2 leads to the compounds B(C2H5)2 (8a-BH3), 2BC2H5 , and 3B . 5a reacts with (1c)2 under simultaneous formation of (C6H5)2PH (7) or (C6H5)PH-HBC8H14 (7-1c) and (C6H5)2POBC8H14 (8c) or (C6H5)2P(OBC8H14)-HBC8H14 (8c-1c). - 6 reacts with tetraethyldiboroxane (11a) to form a mixture of the oligomeric compounds - n - (6'a)n.

Dimeric (Dihalogenoaluminiooxy)diorganoboranes

Tetraorganodiboroxanes R2BOBR2 (1) 2 = 1,5-cyclooctanediyl = C8H14> and aluminium trihalides AlHal3 (2) n: Hal = Cl, (2b)2: Hal = Br> eliminate halogenodiorganoboranes R2BHal (4) in yields >90percent to give crystalline, in solution and in the solid state dimeric (dihalogenoaluminiooxy)diorganoboranes (Hal2AlOBR2)2 (3xy)2 2: R = C2H5, Hal = Cl; (3ba)2: R2 = C8H14, Hal = Cl; (3ab)2: R = C2H5, Hal = Br; (3bb)2: R2 = C8H14, Hal = Br>, having two AlOAl bonds . - The X-ray analyses of (3aa)2 and (3bb)2 confirmed the four-membered AlOAlO ring with the exocyclic O-diorganoboryl groups.

ORGANOBORANES. XXXIII. PROTONOLYSIS OF TRIETHYLBORANE WITH CARBOXYLIC ACIDS

The hydrolysis of triethylborane with water proceeds very slowly at room temperature, unaffected by hydrochloric acid, but inhibited by sodium hydroxide.Acetic acid, however, removes the first ethyl group rapidly, followed by a slower removal of the second.The protonolysis of the third ethyl group requires elevated temperatures.The unusual reactivity of carboxylic acid toward protonolysis of triethylborane is attributed to the presence of both acidic and basic sites in close proximity.The effect of added reagents is also studied.Thus, bases, such as pyridine, inhibit the removal of the first ethyl group, whereas, hydroxylic solvents, water, and strong acids and bases hinder protonolysis of the second ethyl group.