155510-81-9Relevant articles and documents
Convenient synthesis of α,β-unsaturated γ-butyrolactones and γ-butyrolactams via decarboxylative iodination of paraconic acids and β-carboxyl-γ-butyrolactams using 1,3-diiodo-5,5-dimethylhydantoin
Phae-Nok, Supasorn,Kuhakarn, Chutima,Pohmakotr, Manat,Reutrakul, Vichai,Soorukram, Darunee
, p. 11087 - 11095 (2015)
A convenient synthetic approach to α,β-unsaturated γ-butyrolactones and α,β-unsaturated γ-butyrolactams is developed. The reaction proceeds via decarboxylative iodination of paraconic acids and β-carboxyl-γ-butyrolactams, employing 1,3-diiodo-5,5-dimethylhydantoin (DIH) under irradiation, followed by dehydroiodination of β-iodo-γ-butyrolactones and γ-butyrolactams providing good yields of α,β-unsaturated γ-butyrolactones and γ-butyrolactams, which are synthetically useful building blocks in organic synthesis.
A synthesis of γ-trifluoromethyl α,β-unsaturated γ-butyrolactones using CF3SiMe3 as a trifluoromethylating agent
Masusai, Chonticha,Soorukram, Darunee,Kuhakarn, Chutima,Tuchinda, Patoomratana,Pakawatchai, Chaveng,Saithong, Saowanit,Reutrakul, Vichai,Pohmakotr, Manat
, p. 6650 - 6658 (2013/09/24)
A general synthesis of γ-trifluoromethyl α,β-unsaturated γ-butyrolactones is described. The fluoride-catalyzed nucleophilic addition of a trifluoromethyl (CF3) group generated from (trifluoromethyl)trimethylsilane (CF3SiMe3, Ruppert-Prakash reagent) to a masked maleic anhydride 1 (cyclopentadiene-maleic anhydride adduct) provides the corresponding adducts 2 with high stereoselectivity. The γ-trifluoromethyl α,β-unsaturated γ-butyrolactones 4 were obtained after treatment of the adducts 2 with Grignard reagents, followed by flash-vacuum pyrolysis.
