April 26, 2024, 04:11:31 PM
Forum Rules: Read This Before Posting


Topic: Cyclopropanate a polyene?  (Read 2212 times)

0 Members and 1 Guest are viewing this topic.

Offline Enthalpy

  • Chemist
  • Sr. Member
  • *
  • Posts: 4041
  • Mole Snacks: +304/-59
Cyclopropanate a polyene?
« on: January 20, 2011, 02:20:02 PM »
And one more ignorant's question...

How difficult is it to cyclopropanate several double bonds?

The intent is, as usual to produce a rocket fuel, or rocket propellant, with a high energy contents.
In hundreds and thousands of tons, without putting the workers at risk meanwhile, and for cheap - of course.

Such a propellant was used on Soyuz, it was called Syntin:
http://en.wikipedia.org/wiki/Syntin
but was abandoned.

Now I realize that cheap myrcene, obtained from turpentine, would lead to a similar molecule with three cyclopropane rings... But though I have no intuition for chemistry, my little finger tells me that the difficult part isn't the polyene molecule but its transformation into a string of strained rings.

What I've read is called the Simmons-Smith reaction:
http://www.organic-chemistry.org/namedreactions/simmons-smith-reaction.shtm

Picture of myrcene: http://saposjoint.net/Forum/viewtopic.php?f=66&t=2609#p30260
of the polycyclic product: http://saposjoint.net/Forum/viewtopic.php?f=66&t=2609#p30264
(=same thread, two messages lower. See Syntin at the same place)

Thank you!
Marc Schaefer, aka Enthalpy

Sponsored Links