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Regioselective reductive: Elimination of aryloxymethylethynylcarbinols - synthesis of aryloxymethylallenes

✍ Scribed by T Rajamannar; K.K Balasubramanian


Book ID
104217994
Publisher
Elsevier Science
Year
1986
Tongue
French
Weight
178 KB
Volume
27
Category
Article
ISSN
0040-4039

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✦ Synopsis


Exclusive formation of allenes and alkenols during the reduction of aryloxymethylethynylcarbinols and ethynylcarbinols respectively, with lithium aluminiumhydride, is being reported.


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## Abstract Treatment of the sugar hemiacetals 1, 5, 7, 10, 12 and 14 with ArSSAr (Ar = phenyl, 2‐pyridyl, 2‐benzothiazolyl) and trialkylphosphanes affords in an S~N~2 process the corresponding aryl thioglycosides 3, 6, 8, 9, 11, 13, 15 and 16 in good to excellent yields. The reaction can be perfor