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read before you pull that trigger

You: "Replaced the Org Synth reference (which doesn't actually have anything to do with the text)" deletion: Norman Kharasch; Robert B. Langford (1973). "2,4-Dinitrobenzenesulfenyl chloride". Organic Syntheses; Collected Volumes, vol. 5, p. 474.. Please read the article (open access) before you draw conclusions. If necessary, ask a chemist to explain the relevance. It turns out in technical articles, titles sometimes do not fully reflect the content.--Smokefoot (talk) 12:33, 8 January 2019 (UTC)

Thanks for your comment. I did indeed read the Org Synth article before editing. It does not describe dissolving metal reductions anywhere, nor does it describe S-alkylation. It has S-arylation and a way of replacing the benzyl group with a halide, which is not what the text or chemical equation describes. Am I missing something in the article? Yongrenjie (talk) 20:45, 9 January 2019 (UTC)

Ah, now I see that in the discussion section there is a brief mention of alkylation: "2,4-Dinitrophenyl benzyl sulfide has been prepared by the reaction of benzyl chloride with 2,4-dinitrothiophenol", which I missed. Still, it's not really relevant as the Wikipedia page (even before I edited it) wrote: "It is introduced by S-alkylation to give alkyl benzylthioethers", which means a reaction BnSH + RX -> BnSR + HX. That's not what's described in the Org Synth discussion section, though: it describes ArSH + BnCl -> ArSBn + HCl. Please let me know if I interpreted something wrongly - I am an organic chemist, so you can throw terminology at me. Yongrenjie (talk) 21:00, 9 January 2019 (UTC)

Fair enough, but the OS ref is directly related to the preceding two sentences "The compound has been used as a source of the thiol functional group in organic synthesis. It is introduced by S-alkylation to give alkyl benzylthioethers." In any case thanks for the note and best wishes.--Smokefoot (talk) 11:42, 10 January 2019 (UTC)

@Smokefoot: I still don’t agree. The OS ref shows it being used as a source of a sulfenyl chloride -SCl, not a thiol -SH. And there are no alkyl benzyl thioethers in the article, only aryl benzyl thioethers. It would also have been nice if you initially pointed out what you thought was wrong about the edit, instead of insinuating that I didn’t read or understand the article. Having re-read it several times, I still stand by my decision to remove the OS ref. Yongrenjie (talk) 12:47, 10 January 2019 (UTC)

Look at the first step. RSH + ArCl --> RSAr. --Smokefoot (talk) 13:08, 10 January 2019 (UTC)

@Smokefoot: Yes, I saw it. That is S-arylation to give a aryl benzyl thioether, not S-alkylation to give an alkyl benzyl thioether. No doubt they are similar processes, but I don't feel that it's an appropriate reference. Yongrenjie (talk) 14:04, 10 January 2019 (UTC)

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