Home > Community > Mesyl Chloride Reactivity
Upvote

VOTE

Downvote
+ Organic
Posted by
Kalman Bookman

Mesyl Chloride Reactivity

Bill Welden  Follow
I think this is probably steric. You have to be careful with mesylates, especially with the choice of base. I have often experienced that the chloride ion of the amine base displaces the mesylate and you end up with a halide!

More

Upvote

VOTE

Downvote
Benjamin Tsavkegh  Follow
That is great to keep in mind.  I should say this is all theoretical to me.  These are from past homeworks in a class I am to take this semester.  Just trying to get ahead.  I am realizing that I need help with my theory.

This is the next step in the synthetic scheme.  I have to think about this some more, but how is a 5 membered ring more energetically favorable than a 6? 

More

Upvote

VOTE

Downvote
Caleb Rose  Follow
This probably has another name, but it reminds me of a benzylic acid rearrangement. I don't see ring size as a factor.

More

Upvote

VOTE

Downvote
David Wilmshurst  Follow
From what I know  saturated 5 membered are more stable than saturated 6 membered and unsaturated 6 membered are more stable than unsaturated 5 membered because of ring strain.

More

Upvote

VOTE

Downvote