By Norbert De Kimpe, Roland Verhe(auth.)
An updated treatise on heteroallylic halides (?-haloketones, ?-haloaldehydes, and ?-haloimines). provides contemporary learn effects touching on availability of the name compounds, their chemical homes and reactivity towards chosen carbon, nitrogen, oxygen, and sulfur nucleophiles, and their position in smooth natural synthesis.
Content:
Chapter 1 Synthesis and reactivity of ??halogenated ketones (pages 1–119):
Chapter 1 Appendix to bankruptcy 1: Synthesis and reactivity of ??halogenated ketones (pages 121–223):
Chapter 2 ??Halogenated imines (pages 225–277):
Chapter 2 Appendix to bankruptcy 2: ??Halogenated imines (pages 279–368):
Chapter three Synthesis and reactivity of ??halogenated aldehydes (pages 369–449):
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Extra resources for α-Haloketones, α-Haloaldehydes and α-Haloimines
Example text
The interaction between the carbonyl group and the nucleophile is mainly 42 Norbert De Kimpe and Roland VerhC lo\ R-C-CH, I B+ 0 + B' II R-CCH2B' +B electrostatic and the high SN2reactivity is due to polarization interaction caused by the smaller steric requirement of RCO as compared to RCH2. Another interpretation by D e ~ a and r ~Winstein ~ ~ and coworkers270is based upon neighbouring group orbital overlap with the adjacent electron-deficient carbon atom. The transition state for the substitution of a-haloketones is envisaged as including partial bonding of the reagent with the p-orbital of the carbonyl carbon.
Cyclic a-iodoketones are obtained directly by oxidation of olefin-iodine complexes with pyridinium dichromate (PDC), but the reaction failed with linear olefins (equation 99)245. Terminal alkynes react with iodine in methanol in the presence of silver nitrate to give mainly a,a-diiodoketones together with diiodoalkenes and iodoalkynes (equation i00)246. RCECH 12, AgNO3 CHjOH RCOCH12 + RC(I)=CHI + RCIC-I (100) At present the most general method consists of the sequential treatment of enol silyl ethers with silver acetate-iodine followed by triethylammonium fluoride.
Of a-halo carbonyl compounds, alkyl halides and benzyl halides in nucleophilic substitution ~~ Reaction ~~~ ~ ~~~ ~~~~ n-C3H7X PhCH2X XCH2COOEt CH3COCH2X PhCOCHzX Ref, R-CI + KI/acetone 1 R-CI + S203-/waterl R-CI + -OAc/ methanol I R-Br + pyridine/ methanol 1 R-Br + thiourea/ methanol 1 R-CI + -N3/ methanol 1 R-CI + -OCN/ methanol 1 R-CI + -SCN/ methanol 1 197 - 1720 220 35 700 1400 105 000 1600 261 263 - 28 198 228 263 286 56 208 406 261 300 640 - 10 700 262 - 33 210 276 263 75 156 176 263 - 83 40 1 770 263 'Relative reactivity to C3H7.