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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: ashish on July 21, 2017, 04:59:05 AM

Title: Nitrene insertion reaction....is this possible ??
Post by: ashish on July 21, 2017, 04:59:05 AM

here is the question

https://postimg.org/image/l7fqc6ij7/

my first question - how can N have only two bonds ??

assuming one H is missing in the product ..and it is N-H actually in the product .

so the reaction would be ....converstion of NO2 group into nitrene by P(OEt)3 ..after that doing an insertion reaction like this ..

http://www.orgmech.co.uk/mech.php?&Num=259

will this work ??
is there any other method ??

Title: Re: Nitrene insertion reaction....is this possible ??
Post by: wildfyr on July 21, 2017, 09:08:43 AM

I agree with your ideas. That 2 bond N is a typo, it should have an H (that it got from that alkane). And since there is preference for the tertiary spot, I would expect this to be a triplet (radical) nitrene mechanism. The singlet doesn't have much preference for primary, secondary etc that I know of since its a direct insertion.

In real life this would be a pretty messy reaction since nitrenes can undergo intrasystem crossing and give both singlet and triplet products, and neither is that picky about what it attacks.