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Conjugate additions of nucleophiles to the double bond give ß-substituted ethyl triphenylphosphonium salts which can be further reacted by Wittig olefination. Sequential reaction with phthalimide and an aldehyde leads, after hydrazinolysis of the resulting N-allylphthalimide, to 3-substituted allylamines: J. Org. Chem., 46, 3119 (1981). N-Alkyl allylamines can also be prepared from alkylamines: Tetrahedron Lett., 24, 3043 (1983):/n
A variety of heterocyclic systems can be synthesized by conjugate addition and subsequent Wittig condensation: J. Am. Chem. Soc., 86, 2744, 2963 (1964); J. Org. Chem., 33, 2416 (1968). Use of carbon nucleophiles permits synthesis of carbocyclic systems: J. Org. Chem., 30, 2082 (1965)./n
Conjugate addition of organocuprates leads to a new phosphonium salt which can be used in the Wittig olefination. With alkenyl cuprates this provides a stereoselective route to (Z,Z)-1,4-pentadienes: Tetrahedron Lett., 26, 1799 (1985). Sequential reactions, catalyzed by CuBr - Ag2CO3 or CuBr - H2O, with Grignard reagents and Wittig olefination with an aldehyde, have also been reported: J. Org. Chem., 61, 9659 (1996):/n
Hazard Statements: H315-H319-H335
Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P261-P280a-P305+P351+P338-P304+P340-P405-P501a
Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.