November 01, 2024, 02:32:55 AM
Forum Rules: Read This Before Posting


Topic: how to convert a diene into a peroxide?  (Read 5043 times)

0 Members and 1 Guest are viewing this topic.

Offline scorpiofrall

  • Very New Member
  • *
  • Posts: 2
  • Mole Snacks: +0/-0
how to convert a diene into a peroxide?
« on: March 17, 2007, 04:02:01 AM »
i have a steriod molecule which have a diene in one of the rings. if i have to fuctionalise this into a peroxide, what is the way. help me out please.

i have attached the pic. the double bonds at positions 5 and 8,  is to be converted into a 5 membered peroxide linkage(-o-o-).
« Last Edit: March 19, 2007, 03:33:46 AM by scorpiofrall »

Offline alphahydroxy

  • Full Member
  • ****
  • Posts: 194
  • Mole Snacks: +7/-6
  • I'm a lumberjack, and I'm OK !
Re: how to convert a diene into a peroxide?
« Reply #1 on: March 17, 2007, 07:47:50 AM »
I'm not sure exactly what you're asking, you could make it much clearer by illustrating the post with the strucutres of your strating material and what you're hoping to make.

However, I guess you could hydrate an alkene to give the alcohol, then oxidise that up to the peroxide.

Offline Ψ×Ψ

  • Chemist
  • Full Member
  • *
  • Posts: 263
  • Mole Snacks: +8/-4
  • ooh, shiny!
    • carbon-based curiosities
Re: how to convert a diene into a peroxide?
« Reply #2 on: March 17, 2007, 03:03:10 PM »
Schenck ene reaction, maybe?  Just a thought...

Offline Spiryt

  • Regular Member
  • ***
  • Posts: 26
  • Mole Snacks: +1/-0
  • Gender: Male
  • ^_^
Re: how to convert a diene into a peroxide?
« Reply #3 on: March 17, 2007, 05:19:59 PM »
Show what you want to do on a picture ::)
Greets ::)
Jose ino osesek :)
^_^

Offline Custos

  • Full Member
  • ****
  • Posts: 217
  • Mole Snacks: +32/-0
  • Gender: Male
Re: how to convert a diene into a peroxide?
« Reply #4 on: March 19, 2007, 02:01:47 AM »
i have a steriod molecule which have a diene in one of the rings. if i have to fuctionalise this into a peroxide, what is the way. help me out please.
Peroxide or epoxide?

Offline alphahydroxy

  • Full Member
  • ****
  • Posts: 194
  • Mole Snacks: +7/-6
  • I'm a lumberjack, and I'm OK !
Re: how to convert a diene into a peroxide?
« Reply #5 on: March 20, 2007, 06:25:06 AM »
I'm not sure exactly what you're asking, you could make it much clearer by illustrating the post with the structures of your starting material and what you're hoping to make.

Offline Custos

  • Full Member
  • ****
  • Posts: 217
  • Mole Snacks: +32/-0
  • Gender: Male
Re: how to convert a diene into a peroxide?
« Reply #6 on: March 20, 2007, 06:57:46 PM »
There's a 1995 review in Contemporary Organic Synthesis by K.J. McCullough (Synthesis and use of cyclic peroxides) that might be a good starting point (here, but you may need a subscription). Mercury acetate or nitrate treatment of allylic hydroperoxides causes 5-endo cyclization to give the intermediate mercuriated 1,2-dioxolanes (cyclic peroxides) which can be reductively demercuriated to give your peroxide.

Sponsored Links