Abstract
The hydroalumination reaction of cyclopropenylcarbinols initially leads to the alumino-cyclopropylcarbinol derivatives, which is followed by an elimination reaction to give the corresponding substituted dienes as unique isomers and in good yields. The use of LiAlD4 as reducing agent provides stereoselectively substituted deuteriodienes.
Key words
dienes - deuteriodienes - reducing agent - cyclopropane - cyclopropene
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17 General Procedure for the Preparation of Dienes from Cyclopropenylcarbinols 1a -g : LiAlH4 (or LiAlD4 , 1 M solution in Et2 O, 1 mmol) was added to a stirred solution of 1a -g (1 mmol) in 5 mL of benzene at 5 °C. The reaction mixture was then heated to 80 °C for several hours and the sequential reduction and elimination reactions were followed by TLC. When the transformation was complete, 1 M aq solution of HCl (3 mL) was added and the aqueous layer was extracted with Et2 O (3 × 5 mL). The combined organic phases were dried over MgSO4 , filtered and the solvent was removed under reduced pressure. Chromatography on silica gel (eluent: hexane) gave the dienes 4a -k in yields indicated in Table
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