Preparation and reaction of phosphorus peri-bridged naphthalenes and their adducts with Lewis acids

(Isopropylamino)(methyl)diphenylphosphonium iodide

“…Amidophosphonium salts are useful precursors for phosphazenes, which are necessary for the aza-Wittig reaction. They can be synthesized by different methods: addition of alkylhalides or methyltriflate to a phosphorus-nitrogen-single bond (Payne et al, 1965;Mizuta et al, 2007), addition of alkylhalides to a phosphorus-nitrogen double bond (Imrie et al, 1995), via intramolecular addition of alkylhalides (Aladzheva et al, 2003) or via other routes (Demange et al, 2006). We became interested in this class of compounds, because the starting compound Ph 2 PN( i Pr)P(Ph)N( i Pr)H acts as a superb ligand in the chromium catalyzed trimerization of ethene (Peitz et al, 2010).…”

“…For the synthesis of Ph 2 PN( i Pr)P(Ph)N( i Pr)H, see: Peitz et al (2010). For the structures of amidophosphonium salts with similar substituents, see: Payne et al (1965); Imrie et al (1995); Aladzheva et al (2003); Demange et al (2006); Mizuta et al (2007). Table 1 Hydrogen-bond geometry (Å , ).…”

An Oxygen‐peri‐Bridged Quinolinium Cation and Its Monoradical Counterpart

“…peri ‐Bridged naphthalene and quinoline systems are of interest, because they possess a strained four‐membered ring, which opens upon nucleophilic attack to yield new naphthalene derivatives in solution . Numerous research efforts (both theoretical and experimental) have focused on new classes of peri ‐bridged naphthalenes containing carbon, boron, phosphorus, sulfur, , and nitrogen, as the peri ‐bridged atoms. However, only limited experimental evidence has been presented in support of oxygen‐ peri ‐bridged naphthalenes , .…”

Naphthalene and Related Systems peri‐Substituted by Group 15 and 16 Elements

“…Phosphorus species 59 (R = iPr, Et) are synthesised by the reaction of 1,8-dilithionaphthalene with the R 2 NPCl 2 . [47,48] Interestingly, reaction with PhPCl 2 yields diphosphaacenaphthene rac-14. The strained four-membered C 3 P ring in 59 is preserved in reactions with a range of electrophiles and metal fragments as shown in Scheme 29.…”

“…[48,49] In addition, several metallacycles containing platinum and palladium as ring atoms are obtained by ring-expansion reactions. [47][48][49] The series of phosphorus peri-bridged species has been expanded, further derivatives being prepared by a different synthetic strategy, using a sequential lithiation/coupling reaction, as shown in Scheme 30. www.chemeurj.org Very few 1,8,9-tris(phosphorus) anthracenes have been reported in the literature, perhaps mirroring the lack of simple synthetic strategies towards these species. Nevertheless, they are very intriguing species from a bonding and structural point of view, since the middle atom is exposed to double peri-congestion.…”