Access the full text.
Sign up today, get DeepDyve free for 14 days.
Loading next page...
/lp/wiley/novel-results-obtained-by-freezing-berry-pseudorotation-of-XiV8n5swsl
References (25)
-
N. Timosheva, A. Chandrasekaran, T. Prakasha, R. Day, R. Holmes (1996)
Axial Site Occupancy by the Least Electronegative Ligands in Trigonal Bipyramidal Tetraoxyphosphoranes(1).Inorganic chemistry, 35 22
-
R. Berry (1960)
Correlation of Rates of Intramolecular Tunneling Processes, with Application to Some Group V CompoundsJournal of Chemical Physics, 32
-
K. Kajiyama, M. Yoshimune, M. Nakamoto, S. Matsukawa, S. Kojima, K. Akiba (2001)
Highly selective one-pot synthesis of spirophosphoranes exhibiting reversed apicophilicity by oxidation of dianions generated from P-H spirophosphorane.Organic letters, 3 12
-
S. Kojima, K. Kajiyama, K. Akiba (1994)
Characterization of an optically active pentacoordinate phosphorane with asymmetry only at phosphorusTetrahedron Letters, 35
-
R. McDowell, A. Streitwieser (1985)
A theoretical study of model substituted phosphoranes, PH4X: apicophilicities, geometries, and electron densitiesJournal of the American Chemical Society, 107
-
R. Holmes (1978)
A MODEL FOR CALCULATING CONFORMATIONAL ENERGIES IN PENTACOORDINATE PHOSPHORUS COMPOUNDSChemInform, 9
-
F. Westheimer (1968)
Pseudo-rotation in the hydrolysis of phosphate estersAccounts of Chemical Research, 1
-
H. Wasada, K. Hirao (1992)
Theoretical study of the reactions of pentacoordinated trigonal bipyramidal phosphorus compounds: PH5, PF5, PF4H, PF3H2, PF4CH3, PF3(CH3)2, P(O2C2H4)H3, P(OC3H6)H3, and PO5H4-Journal of the American Chemical Society, 114
-
N. Timosheva, T. Prakasha, A. Chandrasekaran, R. Day, R. Holmes (1995)
Pentacoordinated Molecules. 107. Axial Preference of a Phenyl Group in a Trigonal Bipyramidal Tetraoxyphosphorane. A Unique Five-Coordinated GeometryInorganic Chemistry, 34
-
S. Kojima, Y. Doi, M. Okuda, K. Akiba (1995)
FIRST STEREOCHEMICAL CHARACTERIZATION OF CONFIGURATIONALLY STABLE DIASTEREOMERS OF HYPERVALENT STIBORANES (10-SB-5) AND ACCELERATION OF INTRAMOLECULAR PERMUTATION BY DONOR SOLVENTSOrganometallics, 14
-
K. Kajiyama, S. Kojima, K. Akiba (1996)
Synthesis and characterization of intra- and intermolecular hydrogen bonding isomers of PH (apical) phosphoranes bearing a hydroxyl group and their thermal cyclizationTetrahedron Letters, 37
-
S. Trippett (1976)
APICOPHILICITY AND RING-STRAIN IN FIVE-COORDINATE PHOSPHORANESPhosphorus Sulfur and Silicon and The Related Elements, 1
-
M. Nakamoto, S. Kojima, S. Matsukawa, Yohsuke Yamamoto, K. Akiba (2002)
Stereomutation and apicophilicity of diastereomeric spirophosphoranes (10-P-5)Journal of Organometallic Chemistry, 643
-
Gregory Thatcher, A. Campbell (1993)
Phosphonates as mimics of phosphate biomolecules: Ab initio calculations on tetrahedral ground states and pentacoordinate intermediates for phosphoryl transferJournal of Organic Chemistry, 58
-
Peng Wang, Yala Zhang, R. Glaser, A. Reed, P. Schleyer, A. Streitwieser (1991)
The Effects of the First- and Second-Row Substituents on the Structures and Energies of PH4X Phosphoranes. An ab initio StudyChemInform, 22
-
S. Kojima, Ryukichi Takagi, K. Akiba (1997)
EXCELLENT Z-SELECTIVE OLEFIN FORMATION USING PENTACOORDINATE SPIROPHOSPHORANES AND ALDEHYDES. WITTIG TYPE REACTION VIA HEXACOORDINATE INTERMEDIATESJournal of the American Chemical Society, 119
-
秋葉 欣哉 (1999)
Chemistry of hypervalent compounds -
C. Moreland, G. Doak, L. Littlefield, N. Walker, J. Gilje, R. Braun, A. Cowley (1976)
The nature of the fluorine exchange processes in some alkyl- and dimethylaminofluorophosphoranesJournal of the American Chemical Society, 98
-
M. Eisenhut, H. Mitchell, D. Traficante, R. Kaufman, J. Deutch, G. Whitesides (1974)
Pseudorotation in XPF4Journal of the American Chemical Society, 96
-
R. Thatcher, R. Kluger (1989)
Mechanism and Catalysis of Nucleophilic Substitution in Phosphate EstersAdvances in Physical Organic Chemistry, 25
-
S. Kojima, K. Kajiyama, K. Akiba (1995)
Characterization of Enantiomeric Pairs of Optically Active 10-P-5 Phosphoranes with Asymmetry Only at PhosphorusBulletin of the Chemical Society of Japan, 68
-
S. Kojima, K. Kajiyama, M. Nakamoto, K. Akiba (1996)
FIRST CHARACTERIZATION OF A 10-P-5 SPIROPHOSPHORANE WITH AN APICAL CARBON-EQUATORIAL OXYGEN RING. KINETIC STUDIES ON PSEUDOROTATION OF STEREOISOMERSJournal of the American Chemical Society, 118
-
R. Engel (1992)
Handbook of organophosphorus chemistry -
L. Griend, R. Cavell (1983)
Phosphoranes. 12. Synthesis and dynamic NMR study of methyltris(trifluoromethyl)phosphorane, Me(CF3)3PHInorganic Chemistry, 14
-
G. Buono*, J. Llinas (1981)
Oxyphosphoranes with an oxaphospholene ring: analysis of the activation barriers of the isomerization processJournal of the American Chemical Society, 103
- Publisher
- Wiley
- Copyright
- Copyright © 2002 Wiley Periodicals, Inc.
- ISSN
- 1042-7163
- eISSN
- 1098-1071
- DOI
- 10.1002/hc.10072
- Publisher site
- See Article on Publisher Site
Abstract
By freezing Berry pseudorotation of spirophosphoranes with recourse to the rigidity of the Martin bidentate ligand, we successfully prepared configurationally stable enantiomeric pairs of optically active phosphoranes, and could isolate “anti‐apicophilic” C‐apical O‐equatorial (O‐cis) phosphoranes. The effect of σ*PO orbital of the O‐cis phosphorane was investigated both experimentally and theoretically. O‐cis phosphoranes were revealed to be much more electrophilic at the phosphorus atom than O‐trans isomers by experimental studies. The acidity of the α‐proton of an O‐cis benzylphosphorane was found to be higher than that of the corresponding O‐trans isomer. By the reaction of the α‐carbanion of an O‐cis benzylphosphorane with PhCHO, we succeeded in the first isolation and full structural characterization of a 12‐P‐6 phosphate bearing an oxaphosphetane ring, the intermediate in the Wittig type reaction using a 10‐P‐5 phosphorane. © 2002 Wiley Periodicals, Inc. Heteroatom Chem 13:390–396, 2002; Published online in Wiley Interscience (www.interscience.wiley.com). DOI 10.1002/hc.10072
Journal
Heteroatom Chemistry – Wiley
Published: Jan 1, 2002