Benzyl or substituted benzyl phosphorothionothiolates (1a–f) on treatment with anhydrous aluminium chloride in benzene at reflux temperature undergo cleavage of the C-S bond with formation of aromatic ring benzylated products (2a–f) in very good yield.
References
1.
(a) KnolkerH.-J., BaumE., GrafR.; JonesP. G., and SpiessO., Angew. Chem., Int Engl, 1999, 38, 2583.
2.
HiraoT., HatanoB., ImamotoY., and OgawaA., J. Org. Chem., 1999, 64, 7665.
3.
MarshJ.P.Jr., and GoodmanL., J. Org. Chem., 1965, 30, 2491.
4.
The Merck Index, 11th edn, Ed. BudavariS., Merck and Co., INC, New Jersey, 1989, 1167
5.
(a) Dictionary of Organic Compounds, 6th edn, University Press, Cambridge, 1996, 3, 2852
6.
Dictionary of Organic Compounds, 6th edn, University Press, Cambridge, 1996, 1, 698
7.
Dictionary of Organic Compounds, 6th edn, University Press, Cambridge, 1996, 1, 729.
8.
KornblumN., and LurieA. P., J. Am. Chem. Soc., 1959, 81, 2705.
9.
KocienskiP.J.Protecting Groups, 1994, 51–52, George Thieme Verlag, Stuttgart.
10.
DaviesD.I., and WaringC., J. Chem. Soc (C)., 1968, 2332.
11.
PapaD., SchwenkE., and WhitmanB., J. Org. Chem, 1942, 7, 587.
12.
TarbellD.S., and PetropoulosJ. C., J. Am. Chem. Soc., 1952, 74, 244
13.
(a) OlahG. A., Friedel-Crafts Reaction, Part I, 1964, 2, 488
14.
OlahG. A., Friedel-Crafts Reaction, Part I, 1964, 2, 598.
15.
MahatoS.B., J. Indian Chem. Soc., 2000, 77, 175.
16.
(a) RhodesC.N., FranksM., ParkesG. M. B., and BrownD. R., J. Chem. Soc. Chem. Commun., 1991, 804.
17.
LaszloP., and MathyA., Helv. Chim. Acta, 1987, 70, 577.