(Benzene-1,3,5-triyl)tris[phosphine] (C6H3(PH2)(3)) and (benzene-1,3,5-triyl)tris[phosphonic acid] (C6H3[P(O)(OH)(2)](3)). Absence of hydrogen bonding in solid primary phosphines

Reiter SA, Assmann B, Nogai SD, Mitzel NW, Schmidbaur H (2002)
HELVETICA CHIMICA ACTA 85(4): 1140-1150.

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Abstract
The prolonged photo-Arbuzov reaction (3 weeks, Hg lamp) of 1,3,5-trichloro-benzene with a large excess of trimethyl phosphite (as a solvent) at 50degrees gives moderate yields of dimethyl (3,5-dichlorophenyl)phosphon ate (1; 14.5%), tetramethyl (5-chloro-1,3-phenylene)bis[phosphonate] (2; 35.4%), and hexamethyl (benzene-1,3,5-triyl)tris[phosphonate] (3; 30.1%). The products can be separated by fractional distillation. Acid hydrolysis of the esters gives almost quantitative yields of the corresponding phosphonic acids 4-6. Reduction of the esters 1-3 by LiAlH4 in tetrahydrofuran affords the primary phosphines (3,5-dichlorophenyl)phosphine (7; 46.5%), (5-chloro-1,3-phenylene)bis[phosphine] (8; 34.5%) and (benzene-1,3,5-triyl)tris[phosphine] (9; 25.2% yield), In the crude reduction products from 2 (preparation of 8) and from 3 (preparation of 9), (3-chlorophenyl)phosphine and (1,3-phenylene)bis[phosphine], respectively, are observed as by-products. All compounds are characterized by standard analytical, spectroscopic, and (for 1, 7, and 8) structural techniques. The arrangement of the molecules in the crystal structures of 7 and 8 suggest that H-bonding between the primary arylphosphines is virtually insignificant for the packing of the components. This is in marked contrast to the importance of H-bonding for the supramolecular chemistry of arylamines The new primary polyphosphines and polyphosphonic acids are to be employed in the construction of extended arrays.
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Reiter SA, Assmann B, Nogai SD, Mitzel NW, Schmidbaur H. (Benzene-1,3,5-triyl)tris[phosphine] (C6H3(PH2)(3)) and (benzene-1,3,5-triyl)tris[phosphonic acid] (C6H3[P(O)(OH)(2)](3)). Absence of hydrogen bonding in solid primary phosphines. HELVETICA CHIMICA ACTA. 2002;85(4):1140-1150.
Reiter, S. A., Assmann, B., Nogai, S. D., Mitzel, N. W., & Schmidbaur, H. (2002). (Benzene-1,3,5-triyl)tris[phosphine] (C6H3(PH2)(3)) and (benzene-1,3,5-triyl)tris[phosphonic acid] (C6H3[P(O)(OH)(2)](3)). Absence of hydrogen bonding in solid primary phosphines. HELVETICA CHIMICA ACTA, 85(4), 1140-1150.
Reiter, S. A., Assmann, B., Nogai, S. D., Mitzel, N. W., and Schmidbaur, H. (2002). (Benzene-1,3,5-triyl)tris[phosphine] (C6H3(PH2)(3)) and (benzene-1,3,5-triyl)tris[phosphonic acid] (C6H3[P(O)(OH)(2)](3)). Absence of hydrogen bonding in solid primary phosphines. HELVETICA CHIMICA ACTA 85, 1140-1150.
Reiter, S.A., et al., 2002. (Benzene-1,3,5-triyl)tris[phosphine] (C6H3(PH2)(3)) and (benzene-1,3,5-triyl)tris[phosphonic acid] (C6H3[P(O)(OH)(2)](3)). Absence of hydrogen bonding in solid primary phosphines. HELVETICA CHIMICA ACTA, 85(4), p 1140-1150.
S.A. Reiter, et al., “(Benzene-1,3,5-triyl)tris[phosphine] (C6H3(PH2)(3)) and (benzene-1,3,5-triyl)tris[phosphonic acid] (C6H3[P(O)(OH)(2)](3)). Absence of hydrogen bonding in solid primary phosphines”, HELVETICA CHIMICA ACTA, vol. 85, 2002, pp. 1140-1150.
Reiter, S.A., Assmann, B., Nogai, S.D., Mitzel, N.W., Schmidbaur, H.: (Benzene-1,3,5-triyl)tris[phosphine] (C6H3(PH2)(3)) and (benzene-1,3,5-triyl)tris[phosphonic acid] (C6H3[P(O)(OH)(2)](3)). Absence of hydrogen bonding in solid primary phosphines. HELVETICA CHIMICA ACTA. 85, 1140-1150 (2002).
Reiter, SA, Assmann, B, Nogai, SD, Mitzel, Norbert W., and Schmidbaur, H. “(Benzene-1,3,5-triyl)tris[phosphine] (C6H3(PH2)(3)) and (benzene-1,3,5-triyl)tris[phosphonic acid] (C6H3[P(O)(OH)(2)](3)). Absence of hydrogen bonding in solid primary phosphines”. HELVETICA CHIMICA ACTA 85.4 (2002): 1140-1150.
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