Efficient α-chlorination of 2-[(1-oxocyclohex-2-en-2-yl)methyl]-1,3-dicarbonyl Compounds Using Sodium Hypochlorite

Abstract

A rapid and efficient regioselective α-chlorination of a new series of β-dicarbonyl compounds using a commercial solution of sodium hypochlorite in the presence of K 2 CO 3 in THF at 0 °C, is reported. With prolonged reaction times, α-chloro β-keto esters, bearing an acyl moiety, undergo a tandem chlorination-deacylation reaction, affording the corresponding α-chlorinated esters.

A One Pot Synthesis of Dehydrohedione (DHH) from a Hedione® Precursor

“…of either CuBr 2 , or CuCl 2 or CuSO 4 in MeOH at 65°C, with 14 These conditions were preferred, since full conversion was not totally achieved with an equimolar amount of NaOCl and K 2 CO 3 in THF at 0°C (78% yield), in analogy to. [78] Cyanuryl chloride was even less efficient. The corresponding Michael addition to 5a (3.26 mol-equiv.…”

“… These conditions were preferred, since full conversion was not totally achieved with an equimolar amount of NaOCl and K 2 CO 3 in THF at 0 °C (78% yield), in analogy to . Cyanuryl chloride was even less efficient.…”

An efficient one-step synthesis of a new series of multifunctional olefins

“…In the course of our study on the MBH chemistry, we have previously reported that the DMAP-promoted direct C-allylation of β-keto esters and β-diketones with cyclic and acyclic Morita-Baylis-Hillman (MBH) alcohols 1,2 (Scheme 2) [27,28], affording the β-dicarbonyl derivatives 3,4, respectively [29,30]. Furthermore, starting from the derivatives 3, in basic conditions, we have also described their regioselective α-chloration, using sodium hypochlorite [31].…”