10371-49-0Relevant articles and documents
Novel and efficient insertions of carbons carrying O-, S-, and N-Linked substituents: Synthesis of α-alkoxyalkyl, α-(Alkylthio)alkyl, and α-(Carbazol-9-yl)alkyl ketones
Katritzky, Alan R.,Xie, Linghong,Serdyuk, Larisa
, p. 7564 - 7570 (1996)
A wide variety of benzotriazolyl-stabilized anions 2, obtained by the lithiation of 1-(α-alkoxyalkyl)-, 1-[α-(alkylthio)alkyl]-, and 1-[α-(carbazol-9-yl)alkyl]benzotriazoles 1, on reaction with aliphatic and aromatic aldehydes and ketones, followed by rearrangement induced by heating in the presence of zinc bromide, furnish one-carbon-homologated α-alkoxyalkyl, α-(alkylthio)alkyl, and α-(carbazol-9-yl)alkyl ketones 4 in simple one-pot operations in good yields with excellent regioselectivity. In several alkoxymethylene insertions, intermediate 2-alkoxyoxiranes were separated in good yields, demonstrating the epoxide mechanism for the rearrangements and providing a facile approach to poly substituted 2-alkoxyoxiranes, another class of important compounds.
α-Thiocarbonyl synthesis via the FeII-catalyzed insertion reaction of α-diazocarbonyls into S-H bonds
Keipour, Hoda,Jalba, Angela,Tanbouza, Nour,Carreras, Virginie,Ollevier, Thierry
supporting information, p. 3098 - 3102 (2019/03/26)
Fe(OTf)2 was used to catalyze the insertion reaction of α-diazocarbonyls into S-H bonds at 40 °C. A wide range of α-thioesters were obtained in yields up to 96% within 24-48 h from their corresponding α-diazoesters. A variety of thiols were use
REGIOSPECIFIC SYNTHESIS OF α-(PHENYLTHIO)CYCLOALKENONES AND OF α-PHENYL-α-(PHENYLTHIO)KETONES VIA αα-ADDITION OF PHENYLSULPHENYL CHLORIDE TO α-DIAZOKETONES
McKervey, M. Anthony,Ratananukul, Piniti
, p. 117 - 120 (2007/10/02)
Cyclic α-diazoketones react with phenylsulphenyl chloride at room temperature to furnish α-chloro-α-(phenylthio)cycloalkanones which undergo ready dehydrochlorination to α-(phenylthio)cycloalkenones when treated with triethylamine; acyclic, terminal α-diazoketones also furnish α-chloro-α-(phenylthio)adducts which are useful electrophiles in the synthesis of α-phenyl-α-(phenylthio)ketones.