Editing Isothiocyanate (section)

==Synthesis==
Allyl thiocyanate isomerizes to the isothiocyanate:<ref name=JCE>{{cite journal |doi=10.1021/ed048p81 |title=The Preparation and Isomerization of Allyl Thiocyanate. An Organic Chemistry Experiment |date=1971 |last1=Emergon |first1=David W. |journal=Journal of Chemical Education |volume=48 |issue=1 |page=81 |bibcode=1971JChEd..48...81E }}</ref>
:{{chem2|CH2\dCHCH2SCN  ->  CH2\dCHCH2NCS}}

Isothiocyanates can be prepared by treating organic [[dithiocarbamate]] salts with [[lead nitrate]] or [[tosyl chloride]].<ref>{{OrgSynth | author = Dains FB | author2 = Brewster RQ | author3 = Olander CP | title = Phenyl Isothiocyanate | year = 1926 | volume = 6 | pages = 72  | doi = 10.15227/orgsyn.006.0072}}</ref><ref>{{cite journal | last1 = Wong | first1 = R | last2 = Dolman | first2 = SJ | title = Isothiocyanates from tosyl chloride mediated decomposition of in situ generated dithiocarbamic acid salts | journal = The Journal of Organic Chemistry | year = 2007 | volume = 72 | issue = 10 | pages = 3969–3971 | pmid = 17444687 | doi = 10.1021/jo070246n}}</ref>
:[[File:Synthesis phenylisothiocyanate 1.svg|center|frameless|upright=2.7|Synthesis of phenyl isothiocyanate]]

Isothiocyanates may also be accessed by the fragmentation reactions of 1,4,2-oxathiazoles.<ref>{{ cite journal | last1 = O'Reilly | first1 = RJ | last2 = Radom | first2 = L | title = Ab initio investigation of the fragmentation of 5,5-diamino-substituted 1,4,2-oxathiazoles | journal = Organic Letters | year = 2009 | volume = 11 | issue = 6 | pages = 1325–1328 | pmid = 19245242 | doi = 10.1021/ol900109b }}</ref> This methodology has been applied to a polymer-supported synthesis of isothiocyanates.<ref>{{ cite journal | last1 = Burkett | first1 = BA | last2 = Kane-Barber | first2 = JM | last3 = O'Reilly | first3 = RJ | last4 = Shi | first4 = L | title = Polymer-supported thiobenzophenone : a self-indicating traceless 'catch and release' linker for the synthesis of isothiocyanates | journal = Tetrahedron Letters | year = 2007 | volume = 48 | issue = 31 | pages = 5355–5358 | doi = 10.1016/j.tetlet.2007.06.025 }}</ref>