@article {2288, title = {Substituent effects on aryltrifluoroborate solvolysis in water: Implications for Suzuki-Miyaura coupling and the design of stable F-18-labeled aryltrifluoroborates for use in PET imaging}, journal = {Journal of Organic Chemistry}, volume = {73}, number = {12}, year = {2008}, note = {ISI Document Delivery No.: 313RGTimes Cited: 17Cited Reference Count: 41Ting, Richard Harwig, Curtis W. Lo, Justin Li, Ying Adam, Michael J. Ruth, Thomas J. Perrin, David M.}, month = {Jun}, pages = {4662-4670}, type = {Article}, abstract = {Whereas electron withdrawing substituents retard the rate of aryltrifluoroborate solvolysis, electron-donating groups enhance it. Herein is presented a Hammett analysis of the solvolytic lability of aryltrifluoroborates where log(k(solv)) values correlate to sigma values with a rho value of approximately -1. This work provides a predictable rubric for tuning the reactivity of boron for several uses including F-18-labeled PET reagents and has mechanistic implications for ArBF3-enhanced ligandless metal-mediated cross coupling reactions with aryltrifluoroborates.}, keywords = {AMINO-ACIDS, AROMATIC SUBSTITUTION, CHEMISTRY, CHYMOTRYPSIN, CONSTANTS, FLUORIDE, HYDROLYSIS, ORGANOBORON COMPOUNDS, POTASSIUM ARYL, TRIFLUOROMETHYL GROUP}, isbn = {0022-3263}, url = {://000256757100038}, author = {Ting, R. and Harwig, C. W. and Lo, J. and Li, Y. and Adam,Michael J. and Ruth, T. J. and Perrin,David M.} } @article {2288, title = {Substituent effects on aryltrifluoroborate solvolysis in water: Implications for Suzuki-Miyaura coupling and the design of stable F-18-labeled aryltrifluoroborates for use in PET imaging}, journal = {Journal of Organic Chemistry}, volume = {73}, number = {12}, year = {2008}, note = {ISI Document Delivery No.: 313RGTimes Cited: 17Cited Reference Count: 41Ting, Richard Harwig, Curtis W. Lo, Justin Li, Ying Adam, Michael J. Ruth, Thomas J. Perrin, David M.}, month = {Jun}, pages = {4662-4670}, type = {Article}, abstract = {Whereas electron withdrawing substituents retard the rate of aryltrifluoroborate solvolysis, electron-donating groups enhance it. Herein is presented a Hammett analysis of the solvolytic lability of aryltrifluoroborates where log(k(solv)) values correlate to sigma values with a rho value of approximately -1. This work provides a predictable rubric for tuning the reactivity of boron for several uses including F-18-labeled PET reagents and has mechanistic implications for ArBF3-enhanced ligandless metal-mediated cross coupling reactions with aryltrifluoroborates.}, keywords = {AMINO-ACIDS, AROMATIC SUBSTITUTION, CHEMISTRY, CHYMOTRYPSIN, CONSTANTS, FLUORIDE, HYDROLYSIS, ORGANOBORON COMPOUNDS, POTASSIUM ARYL, TRIFLUOROMETHYL GROUP}, isbn = {0022-3263}, url = {://000256757100038}, author = {Ting, R. and Harwig, C. W. and Lo, J. and Li, Y. and Adam,Michael J. and Ruth, T. J. and Perrin,David M.} } @article {411, title = {A diphenylboron chelate of an ethylenebishydroxylamine formaldehyde adduct}, journal = {Acta Crystallographica Section E-Structure Reports Online}, volume = {58}, year = {2002}, note = {ISI Document Delivery No.: 546XWTimes Cited: 3Cited Reference Count: 13Part 5}, month = {May}, pages = {O473-o475}, type = {Article}, keywords = {CRYSTAL, MOLECULAR-STRUCTURES, ORGANOBORON COMPOUNDS}, isbn = {1600-5368}, url = {://000175302500033}, author = {Kliegel, W. and Amt, H. and Patrick, B. O. and Rettig, S. J. and Trotter, J.} } @article {418, title = {A diphenylboron chelate of an N-alkyl-2,2-diarylglycolohydroxamic acid}, journal = {Acta Crystallographica Section E-Structure Reports Online}, volume = {58}, year = {2002}, note = {ISI Document Delivery No.: 598QUTimes Cited: 1Cited Reference Count: 15Part 10}, month = {Oct}, pages = {O1095-O1097}, type = {Article}, abstract = {4-Cyclohexyl-5-[hydroxy-bis(4-methoxyphenyl)methyl]-2,2-diphenyl-1,3-dio xa-4-azonia-2-borata-4-cyclopentene, C34H36BNO5, contains a five-membered heterocyclic ring with a B-envelope conformation. Bond lengths and angles are similar to those in related hydroxamatoboron chelates.}, keywords = {ORGANOBORON COMPOUNDS}, isbn = {1600-5368}, url = {://000178288700067}, author = {Kliegel, W. and Schumacher, U. and Patrick, B. O. and Rettig, S. J. and Trotter, J.} } @article {413, title = {An O-bridged BONBON ring system (phenol adduct)}, journal = {Acta Crystallographica Section E-Structure Reports Online}, volume = {58}, year = {2002}, note = {ISI Document Delivery No.: 536XPTimes Cited: 1Cited Reference Count: 5Part 4}, month = {Apr}, pages = {O371-O373}, type = {Article}, abstract = {1,4-Diphenyl-3,3:6,6-bis(tetramethylene)-2,5,7-trioxa-3,6-diazonia-1,4-d iboratabicyclo[2.2.1]heptanenphenol (1/1), C20H26B2N2O3.C6H5OH, contains a six-membered boat-shaped BONBON ring, with an O bridge forming a bicyclic system. The phenol molecule shows some disorder, and is linked to the heterocycle by an O-H...O hydrogen bond. The molecular dimensions of the heterocycle differ slightly from those of the parent (phenol-free) crystal, presumably as a result of the hydrogen bonding.}, keywords = {CRYSTAL, ORGANOBORON COMPOUNDS}, isbn = {1600-5368}, url = {://000174727400024}, author = {Kliegel, W. and Druckler, K. and Patrick, B. O. and Rettig, S. J. and Trotter, J.} } @article {415, title = {Triphenylboroxin complex with N-cyclohexylhydroxylamine and its isobutyraldehyde nitrone}, journal = {Acta Crystallographica Section E-Structure Reports Online}, volume = {58}, year = {2002}, note = {ISI Document Delivery No.: 589AWTimes Cited: 0Cited Reference Count: 19Part 9}, month = {Sep}, pages = {O1034-O1037}, type = {Article}, abstract = {N-Cyclohexylhydroxylamine(O-B)triphenylboroxin N-cyclohexyl-C-(2-propyl)nitrone hemibenzene hemisolvate, C24H28B3NO4.C10H19NO.0.5C(6)H(6), contains one molecule of N-cyclohexylhydroxylamine in its N-oxide form added to a boroxin heterocycle, with one molecule of N-cyclohexyl-C-(2-propyl)nitrone linked by an O...H-N hydrogen bond to the protonated hydroxylamine moiety, and a molecule of benzene which is located on a centre of inversion.}, keywords = {BORON CHELATE, CRYSTAL, LIGAND, MOLECULAR-STRUCTURES, ORGANOBORON COMPOUNDS, REACTION-PRODUCTS, REARRANGEMENT}, isbn = {1600-5368}, url = {://000177736200049}, author = {Kliegel, W. and Lubkowitz, G. and Patrick, B. O. and Rettig, S. J. and Trotter, J.} } @article {412, title = {Triphenylboroxin N,N-diethylhydroxylamine adduct (dimethylformamide solvate)}, journal = {Acta Crystallographica Section E-Structure Reports Online}, volume = {58}, year = {2002}, note = {ISI Document Delivery No.: 578XXTimes Cited: 3Cited Reference Count: 14Part 8}, month = {Aug}, pages = {o831-o833}, type = {Article}, abstract = {N,N-Diethylhydroxylamine(O-B)triphenylboroxin N,N-dimethylformamide [2-(diethylammoniooxy)-2,4,6-triphenyl-1,3,5-trioxa-4,6-dibora-2-boratac yclohexane N,N-dimethylformamide], C22H26B3NO4.C3H7NO, contains one molecule of N,N-diethylhydroxylamine in its N-oxide form added to a boroxin heterocycle, with N,N-dimethylformamide solvent linked by an O...H-N hydrogen bond to the protonated hydroxylamine moiety.}, keywords = {ORGANOBORON COMPOUNDS}, isbn = {1600-5368}, url = {://000177147300047}, author = {Kliegel, W. and Druckler, K. and Patrick, B. O. and Rettig, S. J. and Trotter, J.} } @article {5107, title = {A BONBON 6-membered ring heterocycle}, journal = {Acta Crystallographica Section E-Structure Reports Online}, volume = {57}, year = {2001}, note = {ISI Document Delivery No.: 480GNTimes Cited: 0Cited Reference Count: 10Part 10}, month = {Oct}, pages = {o943-o944}, type = {Article}, abstract = {2,5-Dimethyl-3,3,6,6-tetraphenyl-1,4-dioxa-2,5-diazonia-3,6- diboratacyclohexane, C26H28B2N2O2, occupies a crystallographic inversion centre, and contains a six-membered BONBON heterocyclic ring, with a chair conformation and dative B-N bonds of length 1.640 (1) Angstrom.}, keywords = {CRYSTAL, MOLECULAR-STRUCTURE, ORGANOBORON COMPOUNDS}, isbn = {1600-5368}, url = {://000171453800047}, author = {Kliegel, W. and Preu, L. and Riebe, U. and Patrick, B. O. and Rettig, S. J. and Trotter, J.} } @article {5106, title = {An OBONC five-membered heterocycle}, journal = {Acta Crystallographica Section E-Structure Reports Online}, volume = {57}, year = {2001}, note = {ISI Document Delivery No.: 487NMTimes Cited: 2Cited Reference Count: 19Part 11}, month = {Nov}, pages = {O1120-O1122}, type = {Article}, abstract = {4-[(2-Hydroxy-1-naphthyl)methyl]-2,2,5-triphenyl-1,3-dioxa-4-azonia-2-bo ratacyclopent-4-ene ethanol solvate, C30H24BNO3.C2H6O, contains a five-membered O-B-O-N=C ring, which is nearly planar (slight B-envelope).}, keywords = {ACIDS, CHELATE, CRYSTAL, MOLECULAR-STRUCTURE, ORGANOBORON COMPOUNDS}, isbn = {1600-5368}, url = {://000171881800082}, author = {Kliegel, W. and Metge, J. E. and Patrick, B. O. and Rettig, S. J. and Trotter, J.} } @article {5105, title = {Structural studies of organoboron compounds, LXXIII. Formation of heterocyclic arylboronates by thermally induced 1,4-aryl migration in diarylboron chelates of C-(1-hydroxyalkyl)nitrones. Crystal and molecular structures of some of the rearrangement produ}, journal = {Canadian Journal of Chemistry-Revue Canadienne De Chimie}, volume = {79}, number = {2}, year = {2001}, note = {ISI Document Delivery No.: 418RJTimes Cited: 2Cited Reference Count: 33}, month = {Feb}, pages = {226-237}, type = {Article}, abstract = {{Synthesis of heterocyclic arylboronates has been carried out by thermally induced rearrangement of diarylboron chelates of C-(1-hydroxyalkyl)nitrones. The structures have been determined from spectroscopic data and from X-ray analyses. Thermoanalytical and time-dependent NMR measurements give information on the nature of the isomerization reaction. Crystal data (at 293 K for 2j, 180 K for the others): 1m, monoclinic, P2(1)/n}, keywords = {ACIDS, arylboronates, C-(1-hydroxyalkyl) nitrones, crystal structures, diarylboron chelates, heterocyclic, ORGANOBORON COMPOUNDS, REARRANGEMENT}, isbn = {0008-4042}, url = {://000167904900016}, author = {Kliegel, W. and Lubkowitz, G. and Pokriefke, J. O. and Rettig, S. J. and Trotter, J.} } @article {4850, title = {Structural studies of organoboron compounds, Part 72 - Nitrones and oximes of bifunctional carbonyl compounds and their reaction products with diarylborinic acids. Crystal and molecular structure of examples of five-, six-, and seven-membered boron chelat}, journal = {Canadian Journal of Chemistry-Revue Canadienne De Chimie}, volume = {78}, number = {10}, year = {2000}, note = {ISI Document Delivery No.: 366QGTimes Cited: 9Cited Reference Count: 74}, month = {Oct}, pages = {1325-1344}, type = {Article}, abstract = {{Synthesis has been carried out of diarylboron chelates of 2- and 3-hydroxynitrones, of 2- and 3-hydroxyoximes, and of 2-carboxynitrones and a 2-carboxyoxime. The structures have been determined from spectroscopic data and from X-ray analyses of 5d, 9a, 11b, and 19. Crystals (at 180 K) of 5d are monoclinic}, keywords = {carboxynitrones, carboxyoximes, CHEMISTRY, COBALT(III), crystal structure, DERIVATIVES, diarylboron chelates, DIPHENYLBORINIC ACID, hydroxynitrones, HYDROXYOXIME STRUCTURE, hydroxyoximes, LIGAND, METAL-COMPLEXES, N-(2-HYDROXYALKYL)NITRONES, ORGANOBORON COMPOUNDS, RING-CHAIN ISOMERISM}, isbn = {0008-4042}, url = {://000090015600009}, author = {Kliegel, W. and Lubkowitz, G. and Pokriefke, J. O. and Rettig, S. J. and Trotter, J.} } @article {4561, title = {Reaction of diphenylborinic acid with pyridinium and phosphonium bisacyl methylides. Crystal and molecular structures of resulting B,N- and B,P-betaines}, journal = {Canadian Journal of Chemistry-Revue Canadienne De Chimie}, volume = {77}, number = {4}, year = {1999}, note = {ISI Document Delivery No.: 204JXTimes Cited: 8Cited Reference Count: 27}, month = {Apr}, pages = {439-450}, type = {Article}, abstract = {{Reaction of pyridinium and phosphonium 2-carboxy-1-formyl-2-oxoethylides with oxybis(diphenylborane) yields 5-(2-oxo-1-(pyridinio or phosphonio)ethylidene)-2,2-diphenyl-1,3-dioxa-2-borata-4-cyclopentanones , which represent novel types of boron nitrogen and boron phosphorus betaines, respectively. Crystals of 5-(2-oxo-1-pyridinioethylidene)-2,2-diphenyl-1,3-dioxa-2-borata-4-cyclop entanone, 1a, are monoclinic}, keywords = {bisacyl methylide diphenylboron, BOND, BORON, boron nitrogen betaines, boron phosphorus betaines, Chelates, crystal structures, ORGANOBORON COMPOUNDS, phosphonium ylides, pyridinium ylides}, isbn = {0008-4042}, url = {://000080762100005}, author = {Grunefeld, J. and Kliegel, W. and Rettig, S. J. and Trotter, J.} } @article {4309, title = {Aromatic aldonitrones of 2-(hydroxyamino)benzyl alcohol and their cyclic isomers. Crystal and molecular structures of a 1-hydroxy-1,2-dihydro-4H-3,1-benzoxazine, a boron chelate, and its parent nitrone ligand}, journal = {Canadian Journal of Chemistry-Revue Canadienne De Chimie}, volume = {76}, number = {4}, year = {1998}, note = {ISI Document Delivery No.: 101TQTimes Cited: 8Cited Reference Count: 16}, month = {Apr}, pages = {389-399}, type = {Article}, abstract = {{The synthesis of a series of C-aryl-N-[2-(hydroxymethyl)phenyl]nitron 5 (that can also exist under certain conditions as isomeric 1-hydroxy-2-aryl-1,2-dihydro-4H-3,1-benzoxazines 8), via 2-(hydroxyamino)benzyl alcohol, 4, and their subsequent reactions with oxybis(diphenylborane), (Ph2B)(2)O, leading to the 5-(arylmethylene)-7,7-diphenyl-6,8-dioxa 5-azonia-7-borata-5H-6,7,8,9-tetrahydrobenzocycloheptenes 6 are described. Crystals of 1-hydroxy-2-(4-methoxyphenyl)-1,2-dihydro-4H-3,1-benzoxazine, 8b, are monoclinic}, keywords = {1-benzoxazines, 1-hydroxy-2-aryl-1, 2-dihydro-4H-3, C-aryl-N-[2-(hydroxymethyl)phenyl]nitrones, COMPOUNDS, crystal structures, METABOLITES, organoboron, ORGANOBORON COMPOUNDS}, isbn = {0008-4042}, url = {://000074884600003}, author = {Kliegel, W. and Metge, J. and Rettig, S. J. and Trotter, J.} } @article {4310, title = {Structural studies of organoboron compounds LXIX - Reaction of ketoximes with aliphatic aldehydes and diphenylborinic acid. Crystal and molecular structure of a diphenylboron chelate derived from the pivaldehyde adduct to cyclohexanone oxime}, journal = {Canadian Journal of Chemistry-Revue Canadienne De Chimie}, volume = {76}, number = {12}, year = {1998}, note = {ISI Document Delivery No.: 180RKTimes Cited: 1Cited Reference Count: 15}, month = {Dec}, pages = {1789-1795}, type = {Article}, abstract = {{Various ketoximes have been reacted with aliphatic aldehydes in the presence of oxybis(diphenylborane) in order to assess the influence of increasingly bulky residues on the nature of the products. Crystals of 5-tert-butyl-2-cyclohexylidene-3,3 -diphenyl-1,4-dioxa-2-azonia-3-boratacyclopentane, 4c, are monoclinic}, keywords = {crystal structure, ketoximes, ORGANOBORON COMPOUNDS}, isbn = {0008-4042}, url = {://000079398800001}, author = {Kliegel, W. and Riebe, U. and Rettig, S. J. and Trotter, J.} } @article {4023, title = {Synthesis of C-aryl-N-(2-hydroxyphenylmethyl)-nitrones and their reaction with diphenylborinic or carboxylic acid derivatives. Crystal and molecular structures of a free nitrone ligand and its diphenyl-boron chelate}, journal = {Canadian Journal of Chemistry-Revue Canadienne De Chimie}, volume = {75}, number = {12}, year = {1997}, note = {ISI Document Delivery No.: YU603Times Cited: 6Cited Reference Count: 62}, month = {Dec}, pages = {1830-1843}, type = {Article}, abstract = {{The syntheses of a number of aromatic aldonitrones of N-(2-hydroxyphenylmethyl)hydroxylamine and their subsequent reactions with diphenylborinic or carboxylic acid derivatives are reported. Crystals of 8-(4-dimethylaminophenylmethylene)-6,6-diphenyl-5,7-dioxa-8-azonia-6-bor ata-5H-6,7,8,9-tetrahydrobenzocycloheptene, 2b, are triclinic}, keywords = {2-METHYLINDOLE, ALDEHYDES, aromatic aldonitrones, C-13 NMR-SPECTRA, crystal structures, HYDROGEN-BOND, N-(2-HYDROXYALKYL)NITRONES, N-(3-HYDROXYALKYL)NITRONES, N-OXIDE, NITROSOBENZENES, ORGANOBORON COMPOUNDS, RING-CHAIN ISOMERISM}, isbn = {0008-4042}, url = {://000071734500005}, author = {Kliegel, W. and Metge, J. and Rettig, S. J. and Trotter, J.} } @article {7350, title = {TRANSANNULAR N-]B BOND FORMATION IN 1,3,5-TRIOXA-6,8-DIAZA-2,4-DIBORACYCLOOCTANES - STRUCTURAL CHARACTERIZATION OF FROZEN INTERMEDIATES IN THE TRANSITION FROM AN 8-MEMBERED MONOCYCLIC SYSTEM TO A BRIDGED RING BICYCLO[3.3.0]OCTANE}, journal = {Molecular Crystals and Liquid Crystals}, volume = {219}, year = {1992}, note = {ISI Document Delivery No.: JD451Times Cited: 1Cited Reference Count: 1310TH INTERNATIONAL CONF ON THE CHEMISTRY OF THE ORGANIC SOLID STATE ( ICCOSS 10 )JUL 07-12, 1991VANCOUVER, CANADACHEM INST CANADA, NAT SCI \& ENGN RES COUNCIL CANADA, PETR RES FUND, UNIV BRIT COLUMBIA, BRUKER SPECTROSPIN CANADA, CHEMAGNETICS, DOTY SCI, GORDON \& BREACH SCI PUBL}, pages = {101-104}, type = {Proceedings Paper}, keywords = {BORON COMPOUNDS, CRYSTAL STRUCTURE ANALYSIS, INCIPIENT NUCLEOPHILIC ADDITIONS, ORGANOBORON COMPOUNDS, TRANSANNULAR N-]B BONDS}, isbn = {0140-6566}, url = {://A1992JD45100010}, author = {Rettig, S. J. and Trotter, J. and Kliegel, W. and Lubkowitz, G.} }