styrene to phenylacetic?

[Hansje]

Late last night, not completely sober, I was pondering the possibility of forming the pseudonitrosite of plain styrene, decomposing it and reducing the resulting nitrostyrene to phenyl acetaldehyde and oxidising the latter to phenylacetic acid. This morning I miraculously remembered my musings of the night before. I tried, but couldn't find anything using TFSE, so it's probably a stupid idea. Before I look any further I'd like to know if it really is and, if so, why.
Anybody?
Hansje high in proteine and fibre!

[Elementary]

Post 258134 (missing)

(foxy2: "New preparation of phenylacetic acid", Chemistry Discourse)

Nobodys home

[Aurelius]

aurelius is just finishing up a styrene to phenylacetic acid with mass-spec analysis to boot.  so far, just have the sodium salt of the final product but a GOOD yeild seems to be in order.  haven't done any weighings of the salt so yeilds are still up in the air.  used the procedure at Rhodium's site

https://www.thevespiary.org/rhodium/Rhodium/chemistry/willgerodt.html

with a couple of variations (very minor)  when completely done a write up will be posted. 

Over-all, aurelius can say this- stinky, but VERY EASY.

[Hansje]

Well, morpholine is out of the question for me and the S + NH4OH thing sounds pretty noxious. So my question, why not pseudonitrosite, remains unanswered.
Hansje high in proteine and fibre!

[PrimoPyro]

You think ammonia is more noxious than nitric oxide fumes? Oh man are you in for a surprise.
Vivent Longtemps La Ruche!

[Rhodium]

PP: It is not the ammonia, but the copious quantities of H2S generated in the Willgerodt reaction that is the "problem". I'd choose a pseudonitrosite reaction in my kitchen over a willgerodt in my garage any day of the week.

[Hansje]

I'd choose a pseudonitrosite reaction in my kitchen over a willgerodt in my garage any day of the week.

I wholeheartedly agree.

You think ammonia is more noxious than nitric oxide fumes? Oh man are you in for a surprise.

No, I don't think that and I won't be surprised by any fumes. I'll pass 'm over NaOH solution, which will readily absorb it to form NaNO2 again. Cleans up most noxiousness. Very economic too.
Hansje high in proteine and fibre!