TY - JOUR
T1 - Synthesis and structure of sterically crowded triarylphosphine bearing 4-bromo-2,6-bis(4-tert-butylphenyl)phenyl group
AU - Sasaki, Shigeru
AU - Izawa, Masatoshi
AU - Yoshifuji, Masaaki
N1 - Funding Information:
This work was supported by JSPS KAKENHI Grant numbers 15550025, 17310063 and 25600020.
Publisher Copyright:
© 2014 Taylor & Francis Group, LLC.
PY - 2014/8/15
Y1 - 2014/8/15
N2 - A novel sterically crowded triarylphosphine bearing a 2,6-diaryl-4-bromophenyl group, [4-bromo-2,6-bis(4-tert-butylphenyl)phenyl]bis(2,4,6-triisopropylphenyl)phosphine (1), was synthesized. The X-ray crystallography revealed that the bond angles and lengths around the phosphorus atom (110.9°, 1.846 Å) are comparable to those of tris(2,4,6-triisopropylphenyl)phosphine and its derivatives. Triarylphosphine 1 is reversibly oxidized to the radical cation at the potential close to that of the typical sterically crowded (bromoaryl)phosphine, (4-bromo-2,6-diisopropylphenyl)bis(2,4,6-triisopropylphenyl)phosphine, and exhibits the UV absorption at long wavelength (max 332 nm) characteristic of the sterically crowded triarylphosphines. Thus, triarylphosphine 1 can be regarded to be a promising candidate for the key synthetic intermediate or building block to the functional molecules bearing sterically crowded triarylphosphine moieties.
AB - A novel sterically crowded triarylphosphine bearing a 2,6-diaryl-4-bromophenyl group, [4-bromo-2,6-bis(4-tert-butylphenyl)phenyl]bis(2,4,6-triisopropylphenyl)phosphine (1), was synthesized. The X-ray crystallography revealed that the bond angles and lengths around the phosphorus atom (110.9°, 1.846 Å) are comparable to those of tris(2,4,6-triisopropylphenyl)phosphine and its derivatives. Triarylphosphine 1 is reversibly oxidized to the radical cation at the potential close to that of the typical sterically crowded (bromoaryl)phosphine, (4-bromo-2,6-diisopropylphenyl)bis(2,4,6-triisopropylphenyl)phosphine, and exhibits the UV absorption at long wavelength (max 332 nm) characteristic of the sterically crowded triarylphosphines. Thus, triarylphosphine 1 can be regarded to be a promising candidate for the key synthetic intermediate or building block to the functional molecules bearing sterically crowded triarylphosphine moieties.
KW - Triarylphosphine
KW - UV-Vis spectrum
KW - X-ray crystallography
KW - bromo group
KW - oxidation potential
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U2 - 10.1080/10426507.2014.907291
DO - 10.1080/10426507.2014.907291
M3 - Article
AN - SCOPUS:84910135692
VL - 189
SP - 1207
EP - 1215
JO - Phosphorus, Sulfur and Silicon and the Related Elements
JF - Phosphorus, Sulfur and Silicon and the Related Elements
SN - 1042-6507
ER -