Keywords
dienes
free-radical addition
magnesium phosphide
phobanes
phosphines
Abstract
Reactions of cycloocta-1,5-diene and (R)-limonene with PH3 result in formation of bicyclic secondary phosphines, applicable in the synthesis of terniary phosphine ligands. To avoid the problems of storage and handling of PH3, we suggest the use of Mg3P2 in its available form, Magtoxin®, as a phosphine source. Higher yields of the target products were confirmed by DFT modeling of the multistep free-radical addition of PH3 to cyclic dienes with the assumption of intramolecular hydrogen transfer at a rate-limiting step.
Funders
Russian Science Foundation
21-73-30010P
References
1.
Torres G.M., Frauenlob R., Franke R., Börner A.
Catalysis Science and Technology,
2015
2.
Slaugh L.H., Mullineaux R.D.
Journal of Organometallic Chemistry,
1968
3.
ref-10.71267-mendc7407-1-3-1-0
L. H. Slaugh and R. D. Mullineaux
1966
4.
ref-10.71267-mendc7407-1-4-1-0
J. L. van Winkle, R. C. Morris and R. F. Mason
1969
5.
ref-10.71267-mendc7407-1-5-1-0
R. F. Mason and J. L. van Winkle
1968
6.
Crause C., Bennie L., Damoense L., Dwyer C.L., Grove C., Grimmer N., Rensburg W.J., Kirk M.M., Mokheseng K.M., Otto S., Steynberg P.J.
Dalton Transactions,
2003
7.
Carreira M., Charernsuk M., Eberhard M., Fey N., Ginkel R.V., Hamilton A., Mul W.P., Orpen A.G., Phetmung H., Pringle P.G.
Journal of the American Chemical Society,
2009
8.
ref-10.71267-mendc7407-1-8-1-0
J. P. Steynberg, K. Govender and P. J. Steynberg
2004
9.
Polas A., Wilton-Ely J.D., Slawin A.M., Foster D.F., Steynberg P.J., Green M.J., Cole-Hamilton D.J.
Dalton Transactions,
2003
10.
Robertson A., Bradaric C., Frampton C.S., McNulty J., Capretta A.
Tetrahedron Letters,
2001
11.
RAUHUT M.M., CURRIER H.A., SEMSEL A.M., WYSTRACH V.P.
Journal of Organic Chemistry,
1961
12.
Hood T.M., Lau S., Webster R.L.
Journal of the American Chemical Society,
2022
13.
ref-10.71267-mendc7407-1-13-1-0
14.
Lewis K.A., Tzilivakis J., Warner D.J., Green A.
Human and Ecological Risk Assessment (HERA),
2016
15.
Alvey L.J., Rutherford D., Juliette J.J., Gladysz J.A.
Journal of Organic Chemistry,
1998
16.
Laikov D.N.
Chemical Physics Letters,
1997
17.
Proudfoot A.T.
Clinical Toxicology,
2009