Thionophosphine Sulfides. I. Preparation and Use in the Friedel-Crafts Reaction¹

Abstract

A convenient new method for the preparation of thionophosphine sulfides is described. These compounds undergo a modified FriedelLCrafts reaction with benzene and provide a route for the synthesis of unsymmetrical phosphinodithioic acids, unobtainable from reactions employing phosphorus pentasulfide (P&o).

Phosphorus Acids as Highly Efficient Promoters for the Palladium‐Phenanthroline Catalyzed Carbonylation of Nitrobenzene to Methyl Phenylcarbamate†

“…General Procedure [7] [Pd(Phen) 2 ][OTf] 2 , [14] [PhenH] [PF 6 ], [39] and Ph 2 P(S)SH [40] were prepared as reported in the literature. (4-MeC 6 H 4 ) 2- [41] and (4-ClC 6 H 4 ) 2 P(O)OH [42] were synthesized by the method of Kosalapoff and Struck, [43] but employing H 2 O 2 as the oxidant in place of Br 2 , as also reported in ref.…”

The Syntheses and Characterization of New Dithiophosphonates derived from Novel 2,4-Bis(methoxytolyl)-1,3-dithia-2,4-diphosphetane 2,4- disulfides and Their Ni(II) Complexes

“…This procedure has been used ever since with various aromatic and aliphatic hydrocarbons instead of cyclohexane (6). In fact, there are two other routes to prepare PTPA compounds (7,8), but they are relatively more difficult and tiresome, not to mention a number of side-products.…”

2,4-Diferrocenyl-1,3-dithiadiphosphetane 2,4-disulfide; structure and reactions with catechols and [PtCl2(PR3)2](R = Et or Bun)

“…Apart from signals due to 1 and 3 (6 15.6 and 16.9 respectively) an AX spectrum [ S 15.8, 16.4, 2J(31P-31P) = 7 Hz] which is readily assigned to the mixed species, 2-(1,l'dimethylferrocen-3-yl)-4-(p-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide 4 was also observed. The formation of 4 in the NMR tube suggests that in solution both 1 and 3 undergo dissociation to form dithiophosphine ylides which can then reversibly form 4 O( 1 )-P-s 11432) s-P-C (7) 115.8(2) 0(2)-P-C (7) 106.2(2) 0(2)-C(2)-C(l) 112.5 (5) Table 3 Selected bond lengths (A) and angles (") in compound 7…”