75759-35-2Relevant academic research and scientific papers
Product Formation and Identification in the Reaction of 6-endo-Hydroxy-5-exo-iodo-3-exo-phenylnorborn-2-endo-ylcarboxylic Acid γ-Lactone with Silver Toluene-p-sulphonate
Sadikun, Amirin bin,Davies, David I.,Kenyon, Robert F.
, p. 1578 - 1582 (2007/10/02)
The reaction of 6-endo-hydroxy-5-exo-iodonorborn-2-endo-ylcarboxylic acid γ-lactone with silver toluene-p-sulphonate affords 7-syn-hydroxy-3-exo-tosyloxynorborn-6-exo-ylcarboxylic acid γ-lactone as the sole product.A comparable reaction with 6-endo-hydroxy-5-exo-iodo-3-exo-phenylnorborn-2-endo-ylcarboxylic acid γ-lactone affords a mixture of 6-endo-hydroxy-3-exo-phenyl-5-exo-tosyloxynorborn-2-endo-ylcarboxylic acid γ-lactone, 7-syn-hydroxy-5-endo-phenyl-3-exo-tosyloxynorborn-6-exo-ylcarboxylic acid γ-lactone, and 2-exo-hydroxy-4-phenylnorborn-5-en-7-anti-ylcarboxylic acid γ-lactone.Product formation is discussed in terms of possible carbocation intermediates.The latter product is unusual in that the position of the bridgehead C-1 proton in the 1H n.m.r. spectrum is similar to that of the aromatic protons.Product structures were determined by n.m.r. spectroscopic studies, and by chemical conversions.
