On the reaction of bis(phosphothioyl)disul‐fanes with hydroxamic acids, part I: Ionic versus radical reaction pathways

Przychodzeń, Witold; Chojnacki, Jarosław

doi:10.1002/hc.20423

Cited by 11 publications

(1 citation statement)

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“…see: FATTEA, FATTIE, FATVEC (Gray et al, 2004), YESDIY (Łopusiń ski et al, 1991), SIZHUF (Przychodzeń & Chojnacki, 2008) and WAYMEO (Knopik et al, 1993).…”

Section: Figurementioning

confidence: 99%

Crystal structures of eight- and ten-membered cyclic bisanisylphosphonothioyl disulfanes and comparison with their P-ferrocenyl analogues

Przychodzeń

Chojnacki

2018

Acta Cryst E

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Two new crystal structures of eight-and ten-membered cyclic bisanisylphosphonothioyl disulfanes, namely 2,5-bis(4-methoxyphenyl)-1,6,3,4,2 5 ,5 5 -dioxadithiadiphosphocane-2,5-dithione, C 16 H 18 O 4 P 2 S 4 , and 2,5-bis(4-methoxyphenyl)-1,6,3,4,2 5 ,5 5 -dioxadithiadiphosphecane-2,5-dithione, C 18 H 22 O 4 P 2 S 4 , have been determined and compared to structures of the ferrocenyl analogues. The eight-membered rings have similar conformations (TBC) but the tenmembered macrocycles are differently puckered. Structural parameters of the relevant SPSSPS motif have been analysed and are discussed in detail. Compound 1 was refined as an inversion twin and 2 was refined as a twocomponent rotational twin. Chemical contextThe most widely used sulfur-transfer agents for thionation of carbonyl compounds are the four-membered 2,4-dianisyl-1,3-dithiadiphosphetane disulfide dimer [AnP(-S)S] 2 and the 2,4-diferrocenyl-1,3-dithiadiphosphetane disulfide dimer [FcP(-S)S] 2 , i.e. Lawesson reagent LR (Jesberger et al., 2003) and ferrocenyl Lawesson reagent fLR (Foreman et al., 1996). However, thiophosphine oxides (AnPSO or FcPSO) separating as cyclic trimers during thionation reactions are usually unwanted side-products. On the other hand, the corresponding alkoxyphosphinodithioic acids, i.e. An(RO)P(S)SH and Fc(RO)P(S)SH, obtained in a simple reaction between LR or fLR and alcohols, are of considerable interest because they form a plethora of structurally interesting chelate complexes with metal ions (van Zyl & Woollins, 2013).The reactions between Lawesson's reagent and diols/ diphenols have been successfully involved in the preparation of bis(anisylphosphonodithioic) acid derivatives and among them the unique eight-, nine-and ten-membered cyclic bisanisylphosphonothioyl disulfanes (Przychodzeń , 2004). A high-yielding formation of these medium-sized cyclic disulfanes upon oxidation of bis(anisylphosphonodithtioic) acid salts by iodine proceeding without oligomeric by-products may be attributed to their fixed structure, containing the most preferred a zigzag motif of the SPSSPS unit. Slightly modified procedures with respect to the original method have recently been applied for the synthesis of related cyclic bis(ferrocenylphosphonothioyl)disulfanes, e.g. eight-membered 1a (Pillay et al., 2015) and ten-membered 2a (Hua et al., 2017) and their crystal structures have been determined. Here we report ISSN 2056-9890 crystal structures compounds 1 and 2, containing anisyl groups instead of the ferrocenyl moiety. Structural commentaryViews of molecular structures and atom-labeling scheme for 1 and 2 are given in Figs. 1 and 2, respectively. Compound 1 crystallizes in the P4 3 2 1 2 space group with a half-molecule in the asymmetric unit. It follows that the molecule obeys point group symmetry described by Schoenflies symbol C 2 (or symbol 2 in international notation). The related ferrocenyl compound 1a crystallizes in space group C2/c with non-typical three and half independent molecules in the asymmetric unit (Z = 28), which com...

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“…see: FATTEA, FATTIE, FATVEC (Gray et al, 2004), YESDIY (Łopusiń ski et al, 1991), SIZHUF (Przychodzeń & Chojnacki, 2008) and WAYMEO (Knopik et al, 1993).…”

Section: Figurementioning

confidence: 99%

Crystal structures of eight- and ten-membered cyclic bisanisylphosphonothioyl disulfanes and comparison with their P-ferrocenyl analogues

Przychodzeń

Chojnacki

2018

Acta Cryst E

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Phosphorus Derivatives of Hydroxylamines, Oximes and Hydroxamic Acids

Palácios

Santos

Vicario

et al. 2010

Patai's Chemistry of Functional Groups

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This comprehensive chapter, organized in three different sections, includes new topics focused on preparation and synthetic applications of phosphorus functionalized hydroxylamines, oximes and hydroxamic acids. The first section comprises the synthesis of phosphorus O ‐substituted hydroxylamines either through phosphorus‐oxygen or nitrogen‐oxygen single bond formation. The synthesis of N ‐substituted hydroxylamines is also covered in this first section by means of phosphorus‐nitrogen or carbon‐nitrogen bond formation reactions. This section also includes several transformations of phosphorus substituted hydroxylamines including among others: rearrangement, hydrolysis, reduction and oxidation reactions. Functionalized oximes containing phosphorus substituents including O ‐ and C ‐substituted oximes, and oximes with α‐ and β‐phosphorated moieties are covered in a second section. This provides an introduction to the common approaches to synthesize phosphorus substituted oximes, and the application of phosphorated oximes to the preparation of more elaborated compounds have been described. Some of the synthetic applications methods covered in the second section are fragmentation and rearrangement reactions, nucleophilic substitution at the phosphorus atom, intramolecular reactions, radical reactions, reduction of carbon‐nitrogen double bond, oxidation reactions, olefination reactions, dehydratation of oximes. The third section is dedicated to the synthesis and reactivity of phosphorus O ‐, N ‐, and C ‐substituted hydroxamic acid derivatives, spanning the few reports in the literature covering this topic. An extensive and current list of references and a subject index complete the chapter. Phosphorus Substituted Hydroxylamine Derivatives Phosphorus Substituted Oximes Phosphorus Substituted Hydroxamic Acid Derivatives Acknowledgments

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Chemical Shifts and Coupling Constants for C20H17ClN2O2PS

Kumar

2014

Chemical Shifts and Coupling Constants for Phosphorus-31

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On the reaction of bis(phosphothioyl)disul‐fanes with hydroxamic acids, part I: Ionic versus radical reaction pathways

Cited by 11 publications

References 28 publications

Crystal structures of eight- and ten-membered cyclic bisanisylphosphonothioyl disulfanes and comparison with their P-ferrocenyl analogues

Crystal structures of eight- and ten-membered cyclic bisanisylphosphonothioyl disulfanes and comparison with their P-ferrocenyl analogues

Phosphorus Derivatives of Hydroxylamines, Oximes and Hydroxamic Acids

Chemical Shifts and Coupling Constants for C20H17ClN2O2PS

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