[Stainless]

Hello, and greetings everyone. Just found this site and must say that i'm impressed. Others in the chemistry community should be alerted to your presence (for all you Star War fans out there  ).

I am trying to figure out how to put a leaving group on a primary alcohol but not on like 3 other secondary alcohols in my compound. My question: anybody out there know of any tricks for selective halogenation or tosylation? BIG thank you in advance for any and all replies. Later.

[movies]

You can usually achieve this with bulky silyl groups like t-butyldiphenylsilyl (TBDPS).

Might be doable with a tosylate, but it would depend on the exact compound, probably.