Reaction database

Substitution reactions

3,374 reactions: 10 worked examples with a reagent table you can scale, 503 named reactions and 2,861 checked procedures from Organic Syntheses.

1–12 of 12

  1. Mitsunobu reaction: benzyl alcohol + phthalimide → N-benzyl phthalimideSubstitutiondehydration PPh3/DIAD-mediated dehydrative coupling of an alcohol with an acidic pronucleophile (pKa ≲ 13). Worked example · after Mitsunobu 1967 Scale
  2. Williamson ether synthesis: sodium ethoxide + 1-bromobutane → ethyl butyl etherSubstitutionSN2 Textbook SN2 ether-formation. Worked example · after Williamson 1850 Scale
  3. Appel reactionSubstitution The Appel reaction is an organic reaction that converts an alcohol into an alkyl chloride using triphenylphosphine and carbon tetrachloride. Named reaction · Wikipedia
  4. Finkelstein reactionSubstitution The Finkelstein reaction, named after the German chemist Hans Finkelstein, is a type of SN2 reaction (substitution nucleophilic bimolecular reaction) that involves the exchange of one halogen atom for another. Named reaction · Wikipedia
  5. Mitsunobu reactionSubstitution The Mitsunobu reaction is an organic reaction that converts an alcohol into a variety of functional groups, such as an ester, using triphenylphosphine and an azodicarboxylate such as diethyl azodicarboxylate (DEAD) or diisopropyl azodicarboxylate (DIAD). Named reaction · Wikipedia
  6. Vicarious nucleophilic substitutionSubstitution In organic chemistry, the vicarious nucleophilic substitution is a special type of nucleophilic aromatic substitution in which a nucleophile replaces a hydrogen atom on the aromatic ring and not leaving groups such as halogen substituents which are ordinarily encountered in SNAr. Named reaction · Wikipedia
  7. Williamson ether synthesisSubstitutionSN2 The Williamson ether synthesis is an organic reaction, forming an ether from an organohalide and a deprotonated alcohol (alkoxide). Named reaction · Wikipedia
  8. A general procedure for Mitsunobu inversion of sterically hindered alcohols: inversion of menthol. (1S,2S,5R)-5-Methyl-2-(1-methylethyl)cyclohexyl 4-nitrobenzoateSubstitution Org. Synth. Coll. Vol. 9, p. 607; Vol. 73, p. 110 · Dodge et al.
  9. Indium-Catalyzed Heteroaryl–Heteroaryl Bond Formation through Nucleophilic Aromatic Substitution: Preparation of 2-Methyl-3-(thien-2-yl)-1H-indoleSubstitution Org. Synth. Vol. 91, p. 273 · Nagase and Tsuchimoto*
  10. Nucleophilic aromatic substitution of aryl fluorides by secondary nitriles: preparation of 2-(2-methoxyphenyl)-2-methylpropionitrileSubstitution Org. Synth. Vol. 79, p. 209 · Caron et al.
  11. Substitution of aryl halides with copper(I) acetylides: 2-phenylfuro[3,2-b]pyridineSubstitution Org. Synth. Coll. Vol. 6, p. 916; Vol. 52, p. 128 · Owsley and Castro
  12. Substitution reactions of 2-benzenesulfonyl cyclic ethers: tetrahydro-2-(phenylethynyl)-2H-pyranSubstitution Org. Synth. Coll. Vol. 9, p. 688; Vol. 70, p. 157 · Brown and Ley