Michael and anti-Michael additions to benzoyl(trifluoromethyl)acetylene

Abstract

Physical data for 4, 5a, 5b, 7a-e, 8, 9a, 9b, 10a, and 10b (4 pages). Ordering information is given on any current masthead page.(16) In particular, the following pairs of signals for 5a and 5b respectively show chemical shift differences of >0.4 ppm: 18.03 and 18.67, 32.87 and 33.49, and 46.52 and 47.01.

Highly Regioselective Synthesis of Oxindolyl-Pyrroles and Quinolines via a One-Pot, Sequential Meyer–Schuster Rearrangement, Anti-Michael Addition/C(sp3)–H Functionalization, and Azacyclization

“…Thus, the addition of a nucleophile to the α-carbon of an α,β-unsaturated system is commonly known as anti-Michael addition, contra-Michael addition, or abnormal Michael reaction. 2 In fact, the addition of nucleophiles to α,β-unsaturated systems in which strong electron-withdrawing substituents redirect the polarity of the double bonds at β-carbon is also a Michael addition concerning the strong electron-withdrawing group and double bond portion as the Michael acceptor. This concept has been explored under suitable conditions on systems with double bonds activated on both sides, and as a result, few synthetic studies and computational reports are available on anti-Michael addition.…”

“…This concept has been explored under suitable conditions on systems with double bonds activated on both sides, and as a result, few synthetic studies and computational reports are available on anti-Michael addition. 2 − 5 …”

Fluorine-containing alkyl(aryl) vinyl sulfides

“…A similar situation is observed for the addition of thiols to trifluoromethyl-containing alkynes activated by an aldehyde or a keto group. 62 The reaction of 1,1,1-trifluoropropyne with bifunctional thiols proceeds in good yields under mild conditions; in the case, of 2-mercaptoethanol, the reaction proceeds selectively involving the sulfur atom. 63 Nucleophilic addition of methanol (in the presence of sodium methoxide) or morpholine to bis(trifluoromethylthio)acetylene gives rise to mixtures of cis-and trans-isomers of the corresponding vinyl sulfides 27, 28.…”

“…21,130 Cycloaddition of trifluoromethylthioethylene to 2,3-dimethylbuta-1,3-diene occurs under drastic conditions. 62…”

Facile preparation and conversion of 4,4,4-trifluorobut-2-yn-1-ones to aromatic and heteroaromatic compounds

“…However, only a few methods have been reported thus far for their preparation [ 15 – 20 ], including one that appeared in 2020 [ 21 ]. However, they suffer from problems, such as the formation of the desired product 2 only as regioisomeric mixtures [ 15 , 17 ] or the applicability to only one substrate without any extension to other related compounds [ 16 , 18 – 20 ]…”