The decalin shown below can undergo ring expansion. However, this ring expansion is fairly complex because the starting material has three stereogenic centres (*), and hence can exist as four diastereoisomers: two trans-decalins and two cis-decalins; the alkoxide can exist in both the axial and equatorial position. The product is a ten-membered ring which contains a double bond. This double bond can be either cis or trans.
One of the four diastereoisomers cannot fragment, whereas the other three can. Two of them give a
trans double bond and the other a cis one.
Click the diastereoisomers shown below to see which product is formed:
(Can you guess which diastereoisomer does not undergo ring expansion and why?)
NOTE: The mesylate leaving group was used in place of tosylate to enable the calculations to run more smoothly
Click on a star to rate it!
Average rating / 5. Vote count:
No votes so far! Be the first to rate this page.
Let us improve this page!
Thanks for your feedback!