[synthnick]

Hi all
I am currently reading Organic Synthesis the Disconnection Approach, and i am scratching my head over this synthesis of jasmone(workbook p 93). I dont understand how the enone is formed.isn't 4 produced during the reaction?
thanks for any help

[camptzak]

http://www.organic-chemistry.org/namedreactions/favorsky-reaction.shtm

[synthnick]

thank you
I found the paper, and the got CO as a gaseous by product. Also I found that those substrates undergo Ramberg–Bäcklund Rearrangement ( Comprehensive Organic Synthesis vol.3 p. 871)

[opsomath]

I found the paper, and the got CO as a gaseous by product.

Hah! Thank you. I was sitting here trying to figure out how you got the double bond, and had just decided that you would either get stuck at the carboxylic acid (classic Favorsky ring contraction) or decarboxylate to the cyclopentanone (no double bond). I was like, "If only you could extrude CO, instead of going Favorsky, it would be the product right away!"

I guess that's what the xylene's for, to enable heating to gaseous-byproduct temps.

[Archer]

Hi all
I am currently reading Organic Synthesis the Disconnection Approach.

A classic text, everyone who is interested in organic chemistry should read this book.

I think I need to get the second edition as my copy of the first edition is looking very tired.