Reactivity in eliminative cleavage of activated four-membered rings. The behaviour of 3-hydroxythietane derivatives

DJ Young, CJM Stirling

Index: Young, David J.; Stirling, Charles J. M. Journal of the Chemical Society. Perkin Transactions 2, 1997 , # 3 p. 425 - 429

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Abstract

3-Hydroxythietane derivatives undergo retro-aldol ring fission in aqueous sodium hydroxide at a rate determined by the substituent (H or Ph) at the 3 position and by the oxidation state of sulfur. Reactions occur between 4× 104 and 5× 105 times faster than for the open chain analogues. These rate accelerations correlate with an expression of strain energy between 41% and 33% compared with approximately 26% for alkene-forming eliminations of ...

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