Problem: The reaction of thiocyanogen (N≡CS—SC≡N) with  cis -cyclooctene proceeds by anti addition. A  bridged  sulfonium ion  is presumed to be an intermediate. Write a stepwise mechanism for this reaction.       

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The reaction of thiocyanogen (N≡CS—SC≡N) with  cis -cyclooctene proceeds by anti addition.

A  bridged  sulfonium ion  is presumed to be an intermediate. Write a stepwise mechanism for this reaction.     

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Based on our data, we think this problem is relevant for Professor Wiginton's class at OLE MISS.

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Our data indicates that this problem or a close variation was asked in Organic Chemistry - Carey 8th Edition. You can also practice Organic Chemistry - Carey 8th Edition practice problems.