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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: dm164 on March 09, 2008, 10:03:12 PM

Title: Special Cyclopropane
Post by: dm164 on March 09, 2008, 10:03:12 PM
I would like to know if two adjacent carbons can be bonded to an oxygen in a cyclopropane; creating C3H4O. I am not sure if the distance between the oxygen and carbons are too far to make it possible. Another similar to the same idea is if all 3 carbons bond to a single nitrogen (C3H3N) would that also be possible?
Title: Re: Special Cyclopropane
Post by: agrobert on March 09, 2008, 10:53:36 PM
What research have you done for this topic?  Try naming them.  The geometry of these compounds is acceptable but do expect the compounds to be isolated at STP?
Title: Re: Special Cyclopropane
Post by: AWK on March 10, 2008, 02:10:56 AM
do you mean these compounds? They are known
Title: Re: Special Cyclopropane
Post by: macman104 on March 10, 2008, 02:23:46 AM
Quote from: dm164 on March 09, 2008, 10:03:12 PM
I would like to know if two adjacent carbons can be bonded to an oxygen in a cyclopropane; creating C3H4O. I am not sure if the distance between the oxygen and carbons are too far to make it possible. Another similar to the same idea is if all 3 carbons bond to a single nitrogen (C3H3N) would that also be possible?
Do you mean, C2H4O?  As in...an epoxide?  I've attached my own revised pdf.  Just in case you had your formula wrong...

Actually, i just thought of this compound for your C3H4O compound, it's attached as well.  it also meets your criteria of being the cyclopropane

EDIT:  Thanks to AWK for the pdf idea.  I hated making drawings in chemdraw and then having to shrink the huge dimension .PNG files it made, this is much easier :).
Title: Re: Special Cyclopropane
Post by: dm164 on March 10, 2008, 08:19:10 PM
The two drawings macman has provided are correct, but I am not refering to the epoxide in his cyclos.pdf.  I am not sure of how these would be named and I have never heard them to known. I expect that compounds will need pressure and heat in order for their creation, but I do not have any idea of their properties. Well, probably explosive.
I would like to know how stable the bonds would be.
Title: Re: Special Cyclopropane
Post by: macman104 on March 10, 2008, 09:45:51 PM
I've reattached them in this post in one pdf for you.  Also with the name of the oxygen containing compound from chemdraw.  However, it hadn't a clue how to name the nitrogen containing compound, nor how to name the nitrogen compound if it were simply 4 carbons.  I would imagine being able to make the oxygen compound as I'm pretty sure the existence of the bicyclo[1.1.0]butane is known (http://www.orgsynth.com/orgsyn/orgsyn/prepContent.asp?prep=cv6p0133), so the oxygen analog I think would be possible.  However, I've not a clue about the nitrogen compound.
Title: Re: Special Cyclopropane
Post by: sjb on March 11, 2008, 05:14:12 AM
If the nitrogen-containing compound had no nitrogen, I think it's tetrahedrane, or tricyclo[1.1.0.02,4]butane. So a semisystematic name could be monoazatetrahedrane, or monoazatricyclo[1.1.0.02,4]butane ??

http://en.wikipedia.org/w/index.php?title=Tetrahedrane&oldid=192376659 (http://en.wikipedia.org/w/index.php?title=Tetrahedrane&oldid=192376659)

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