The Michael reaction of various nitroalkanes 1 with electro-factant, produces better results. Good yields of the products 3 are obtained even with hindered, and functionalized star-philic alkenes 2 can be performed in NaOH (0.025Οͺ0.1 M), without any organic solvent. In many cases the presence of ting materials. cetyltrimethylammonium chloride (CTACl), as cationic sur-Nucleophilic addition of carbanions to electrophilic al-a large excess of nitroalkane, [4d] or the help of ultrasound [4e] are required. kenes activated by an electron-withdrawing group (the Michael reaction) is one of the most important pro-
The need to accomplish this important synthetic transcedures [1] in organic synthesis for the formation of a new formations under milder conditions and with less toxic and carbonΟͺcarbon bond.
environmentally compatible materials has led us to develop In this context the use of primary and secondary nitroalthis procedure of Michael reaction in aqueous media kanes as carbanions is a valuable tool considering that the (Scheme 1, Table 1). nitro group can be further transformed into various functionalities. [2] As routine procedures, this reaction is performed in the presence of different organic bases in homogeneous solutions [3] or, alternatively, under heterogeneous catalysis. [4] Increasingly demanding environmental legislation, public 1Ψ3 R 1 R 2 EWG and corporate pressure and resulting drive towards clean technology in the chemical industry, with the emphasis on a H CH 3 CO 2 Me b H C 2 H 5 CO 2 Me reduction of waste at source, will require increasing attenc H CH 3 (CH 2 ) 3 CO 2 Me tion on the use of less toxic and environmentally compatible d CH 3 CH 3 CO 2 Me materials in the design of new synthetic methods. [5] e H C 6 H 5 CO 2 Me f H CH 3 CHOH(CH 2 ) 2 CO 2 Me Established chemical processes that are often based on g H CH 3 CN technology developed in the first half of the 20th century, h H C 2 H 5 CN i CH 3 CH 3 CN may no longer be acceptable in these environmentally conj H CH 3 (CH 2 ) 4 CN
scious days. [6]