• N Satish Kumar

      Articles written in Journal of Chemical Sciences

    • Chemistry of selected cyclic P(III) compounds possessing a P-Cl bond

      K C Kumaraswamy Sudha Kumaraswamy Praveen Kommana N Satish Kumar K Senthil Kumar

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      The compounds [CH2(6-t-Bu-4-Me-C6H2O)2]PCl (1), (OCH2CMe2CH2O)-PCl (2), and [ClPN(t-Bu)]2 (3) have been utilized as precursors in the synthesis of (i) new pentacoordinate phosphorus compounds [e.g. CH2(6-t-Bu-4-Me-C6H2O)2 P(NRR′)(O2C6C14), CH2(6-t-Bu-4-Me-C6H2O)2PX[OC(O-i-Pr)N=N(C(O)O-i-Pr)],(ii) cyclic phosphates and their complexes [e.g. imidazolium+CH2(6-t-Bu-4-Me-C6H2O)2PO2-.MeOH], (iii) new cycloaddition products [e.g. CH2(6-t-Bu-4-Me-C6H2O)2PC(CO2Me)C(CO2Me)C(O)N, (iv) macrocyclic compounds [e.g. [(t-BuN)P]2[-OCH2CMe2CH2O-]h2] and (v) phosphonates [e.g. (OCH2CMe2CH2O)P (O)CH2C(CN)=CHC5H4FeC5H5]. The synthetic and structural aspects of these new products are discussed.

    • Unusual products in the reactions of phosphorus(III) compounds with N=N, C≡C or conjugated double-bonded systems

      K C Kumara Swamy E Balaraman M Phani Pavan N N Bhuvan Kumar K Praveen Kumar N Satish Kumar

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      The diversity of products in the reaction of diethyl azodicarboxylate (DEAD)/diisopropyl azodicarboxylate (DIAD) and activated acetylenes with PIII compounds bearing oxygen or nitrogen substituents is discussed. New findings that are useful in understanding the nature of intermediates involved in the Mitsunobu reaction are highlighted. X-ray structures of two new compounds (2-t-Bu-4-MeC6H3O)P (μ-N-t-Bu)2P+[(NH-t-Bu)N[(CO2]-i-Pr)(HNCO2-i-Pr)]](Cl-)(2-t-Bu-4-MeC6H3OH)(23)and [CH2(6-t-Bu-4-Me-C6H2O)2P(O)C(CO2Me)C-(CO2Me)CClNC(O)Cl] (33) are also reported. The structure of23 is close to one of the intermediates proposed in the Mitsunobu reaction.

    • Allenylphosphonates with a 1,3,2-dioxaphosphorinane ring: Synthesis, structures, stability and utility

      N N Bhuvan Kumar Manab Chakravarty N Satish Kumar K V Sajna K C Kumara Swamy

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      Synthesis, structures and stability (thermal and air) of allenylphosphonates of the type (OCH2CMe2CH2O)P(O)C(R)=C=CR'R" and [R"R'C=C=C(R)P(O)(OCH2)2]2C are discussed. Thermally activated dimerization (cycloaddition) of (OCH2CMe2CH2O)P(O)C(H)=C=CMe2 leads to the phosphonocyclobutane [(OCH2CMe2CH2O)P(O)C(H)=]2[C-CMe2]2 (18). Many of these allenes undergo addition of diethylamine to lead to enaminophosphonates that are readily hydrolysed by water to lead to 𝛽-ketophosphonates. The latter compounds are useful as Horner-Wadsworth-Emmons (HWE) reagents. Molecular structures of (OCH2CMe2CH2O)P(O)C(CH2OH)=C=CH2 (6), [H2C=C=C(H)P(O)(OCH2)2]2C (9), (OCH2CMe2CH2O)P(O)CH=C=CH2 (12), [(OCH2CMe2CH2O)P(O)C(H)=]2[C-CMe2]2 (18), and the 𝛽-ketophosphonate (OCH2CMe2CH2O)P(O)CH2)-C(O)CHMe2 (24) have been determined. In compound 6, intermolecular hydrogen bonding between the phosphoryl oxygen and the hydroxyl group leading to an infinite chain is observed. In 6, there is a significant deviation (ca 7°) from the orthogonality expected between the planes containing 4 atoms of (a) H2C=C and (b) C=C(H)P in the allene part. In 9, weak C-H…O interaction between the phosphoryl oxygen atom and a CH2 proton of the six-membered ring is present.

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