• Mandala Anitha

      Articles written in Journal of Chemical Sciences

    • FeCl3 catalysed regioselective allylation of phenolic substrates with (𝛼-hydroxy)allylphosphonates

      Mandala Anitha Ramesh Kotikalapudi K C Kumara Swamy

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      Electrophilic allylation of phenolic substrates including salicylaldehydes with (𝛼-hydroxy) allylphosphonates is presented. It is observed that catalytic FeCl3 is sufficient to accomplish the allylation. Interestingly, the reaction led to the formation of allylphosphonates in addition to vinylphosphonates, depending upon the substituent. The vinylphosphonates obtained here are 𝐸-isomers. More importantly, the reaction occurred regioselectively with respect to the phenolic substrates. Substituted allylphosphonates are formed when salicylaldehyde or (2-hydroxy-phenyl)arylmethanones are used. Conclusive proof for the formation of allylphosphontates as well as vinylphosphonates has been provided by single crystal X-ray crystallography.

    • New reactions of allenes, alkynes, ynamides, enynones and isothiocyanates

      K C KUMARA SWAMY G GANGADHARARAO MANDALA ANITHA A LEELA SIVAKUMARI ALLA SIVA REDDY ADULA KALYANI SRINIVASARAO ALLU

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      Abstract. This perspective article is related to transformations (both catalytic and non-catalytic) involving allenes, alkynes/enynones/ynamides and isothiocyanates. Part of the work from the author’s group has been reviewed along with some new reactions of (i) allenylphosphonate/allenylphosphine oxide and (ii) a P(III) isothiocyanate. Thus, the allenylphosphine oxide Ph2P(O)C(Ph)=C=CH2 undergoes base (DBU) catalyzed addition to the β-ketophosphonate (OCH2CMe2CH2O)P(O)CH2C(O)CH3 at 90°C to afford the addition product Ph2P(O)C(Ph)=C(Me)CH[C(O)Me][P(O)(OCH2CMe2CH2O)]. In an analogous reaction, with DBU as the base at 140°C, isomeric vinylphosphine oxides (Z)-Ph2P(O)C(Ph)=C(Me)CH2[C(O)Me] and (E)-Ph2P(O)C(Ph)=C(Me)CH2[C(O)Me] were isolated. The E-isomer has been characterized by single crystal X-ray structure determination. In another set of studies, the reaction of P(III) isothiocyanate (OCH2CMe2CH2O)P(NCS) with N-(2-bromomethyl)sulfonamide afforded an unusual product with the formula(OCH2CMe2CH2O)P(O)SCH2CH2NHS(O)2-(C6H4-4-Me) as shown by X-ray structure determination. This result is different from that obtained in the recently reported analogous reaction using phenyl isothiocyanate.

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