Reaction of Arylsulfonylhydrazones of Aldehydes with α-Magnesio Sulfones. A Novel Olefin Synthesis
A Kurek-Tyrlik, S Marczak, K Michalak…
Index: Kurek-Tyrlik; Marczak; Michalak; Wicha; Zarecki Journal of Organic Chemistry, 2001 , vol. 66, # 21 p. 6994 - 7001
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Citation Number: 22
Abstract
Reactions of representative tosylhydrazones of aldehydes and ketones with α-metalated sulfones were examined in order to develop a practical olefination method. Treatment of aldehyde tosylhydrazone 2 with an excess of α-lithiated methyl phenyl or dimethyl sulfones yielded 3a. The reaction of 2 with sterically unhindered lithiated alkyl sulfones gave mixtures of the respective olefination products 3b-d along with the Shapiro fragmentation product 4. ...
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