139005-41-7Relevant academic research and scientific papers
An umpolung oxa-[2,3] sigmatropic rearrangement employing arynes for the synthesis of functionalized enol ethers
Gaykar, Rahul N.,George, Malini,Guin, Avishek,Bhattacharjee, Subrata,Biju, Akkattu T.
, p. 3447 - 3452 (2021/05/04)
An oxa-[2,3] sigmatropic rearrangement involving arynes is reported featuring the umpolung of ketones, where the C=O bond polarity is reversed. The in situ-generated sulfur ylides from β-keto thioethers and arynes undergo efficient rearrangement allowing the facile and robust synthesis of functionalized enol ethers in high yields and excellent functional group compatibility. Preliminary mechanistic studies rule out the possibility of Pummerer-type rearrangement operating in this case.
CHEMISTRY OF α-NITROEPOXIDES: SYNTHESIS OF USEFUL INTERMEDIATES VIA NUCLEOPHILIC RING OPENING OF α-NITROEPOXIDES
Vankar, Yashwant D.,Shah, Kavita,Bawa, Anita,Singh, Surendra P.
, p. 8883 - 8906 (2007/10/02)
Various α-nitroepoxides are converted into corresponding 1,2-diketones via two different ways of ring opening viz. with Pd(O) and with DMSO/BF3*EtO2 (or ClSiMe3).In addition to this, a variety of nucleophiles are reacted with α-nitrocyclopentene oxide 6 and α-nitrocyclohexene oxide 7 to form the corresponding α-substituted ketones which are useful intermediates in organic synthesis.Two of the products so obtained viz. 32 and 33 are also transformed further into optically active thialactones 38 and 39 respectively via baker's yeast reduction followed by lactonisation.
