The reaction of 6-chloro-1-hexene 1 with lithium powder and a catalytic amount of 4,4%-di-tert-butylbiphenyl (DTBB, 5% molar) in THF at -78°C gives the corresponding organolithium intermediate 2, which by reaction with different electrophiles [Bu t CHO, PhCHO, Et 2 CO, (CH 2 ) 5 CO, PhCOMe] affords,
✦ LIBER ✦
DTBB-catalysed lithiation of 2,3-dichloropropene and related chloroamines: Synthetic applications
✍ Scribed by Fernando F Huerta; Cecilia Gómez; Albert Guijarro; Miguel Yus
- Book ID
- 103405887
- Publisher
- Elsevier Science
- Year
- 1995
- Tongue
- French
- Weight
- 807 KB
- Volume
- 51
- Category
- Article
- ISSN
- 0040-4020
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Vinylic lithium reagents 1 and 2 could be obtained by the title procedure from their chloro precursors 5 and 6 instead of the less stable corresponding bromo derivatives 3 and 4. Condensation with carbonyl compounds leads to interesting synthetic applications such as a two steps synthesis of retinal