Carboxylic acids are readily reduced to the corresponding aldehydes in high yields by treatment of acyloxy-9-borabicycloC3.3.llnonanes with lithium 9-boratabicycloL3.3.l]nonane (Li 9-BBNH) at room temperature. Thexylchloroborane-methyl sulfide 2 and thexylbromoborane-methyl sulfide 3
Selective reduction of aromatic nitriles to aldehydes by potassium 9-sec-amyl-9-boratabicyclo[3.3.1]nonane
β Scribed by Jin Soon Cha; Mal Sook Yoon
- Publisher
- Elsevier Science
- Year
- 1989
- Tongue
- French
- Weight
- 236 KB
- Volume
- 30
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
The title reducing agent (1) reduces aromatic nitriles to the corresponding aldehydes in yields of 60-98 %, while aliphati? nitriles being intact. Transformation of nitriles to aldehydes is of importance in organic synthesis. Numerous methods have been proposed to achieve this objectiveI; however, there have been no report for the selective reduction of only aromatic nitriles to the corresponding aldehydes in the presence of aliphatic nitriles.
π SIMILAR VOLUMES
## Abstract [^3^H]lithium 9βboratabicyclo[3.3.1]nonane, at specific activity of 52β55 Ci/mmol, was synthesized by reduction of BβOMeβ9βBBN with lithium tritide. Its reducing characteristics were illustrated by the synthesis of [17β^3^H] estradiol, [2β^3^H] dihydrotetrabenazine and 1β(hydroxy[^3^H]m
Asymmetric reduction of a-keto acetals with a chiral borohydride, potassiun 9-0-(1~-isopropylidcnt-5-doxy-a-Dxylofuranosyl)-~~~clo[3.3.l]nonane in 'IHF at -78Β°C provided the corresponding a-hydn-rxy acetals with 87 -99 % ee. Optically active a-hydroxy aldehydes are useful chit-al building blocks for