Editing Thioester (section)

==Thionoesters==
[[Image:Thionoester general structure.png|thumb|class=skin-invert-image|right|150px|General structure of a thionoester, where R and R' are [[organyl]] groups, or [[Hydrogen|H]] in the case of R]]
[[Image:Methyl-thionobenzoate-2D-skeletal.png|thumb|class=skin-invert-image|right|150px|[[Skeletal formula]] of methyl thionobenzoate]]
'''Thionoesters''' are isomeric with thioesters.  In a thionoester, sulfur replaces the carbonyl oxygen in an ester. Methyl thionobenzoate is C<sub>6</sub>H<sub>5</sub>C(S)OCH<sub>3</sub>. Such compounds are typically prepared by the reaction of the [[thioacyl chloride]] with an alcohol.<ref>{{cite book | author = Cremlyn, R. J. | title = An Introduction to Organosulfur Chemistry | publisher = John Wiley and Sons | location = Chichester | year = 1996 | isbn = 0-471-95512-4 }}</ref>

[[Image:Thionoester-from-thioacyl-chloride-2D-skeletal.png|center|class=skin-invert-image|380 px]]

They can also be made by the reaction of [[Lawesson's reagent]] with esters or by treating [[pinner salt]]s with [[hydrogen sulfide]].

Various thionoesters may be prepared through the [[transesterification]] of an existing methyl thionoester with an alcohol under base-catalyzed conditions.<ref>{{cite journal |last1=Newton |first1=Josiah J. |last2=Britton |first2=Robert |last3=Friesen |first3=Chadron M. |title=Base-Catalyzed Transesterification of Thionoesters |journal=The Journal of Organic Chemistry |volume=83 |issue=20 |pages=12784–12792 |date=4 October 2018 |doi=10.1021/acs.joc.8b02260|pmid=30235418|s2cid=52309850 }}</ref>

[[Image:Transesterification of Thionoesters.png|center|class=skin-invert-image|380px]][[Xanthate]]s<ref>{{Cite journal |last1=Monteith |first1=John J. |last2=Scotchburn |first2=Katerina |last3=Mills |first3=L. Reginald |last4=Rousseaux |first4=Sophie A. L. |date=2022 |title=Ni-Catalyzed Synthesis of Thiocarboxylic Acid Derivatives |url=https://doi.org/10.1021/acs.orglett.1c04074 |journal=Organic Letters |volume=24 |issue=2 |pages=619–624|doi=10.1021/acs.orglett.1c04074 |pmid=34978834 |s2cid=245669904 |url-access=subscription }}</ref> and [[thioamide]]s<ref>{{Cite journal |last1=Liu |first1=Yinbo |last2=Mo |first2=Xiaofeng |last3=Majeed |first3=Irfan |last4=Zhang |first4=Mei |last5=Wang |first5=Hui |last6=Zeng |first6=Zhuo |date=2022 |title=An efficient and straightforward approach for accessing thionoesters ''via'' palladium-catalyzed C–N cleavage of thioamides |url=http://dx.doi.org/10.1039/d1ob02349g |journal=Organic & Biomolecular Chemistry |volume=20 |issue=7 |pages=1532–1537 |doi=10.1039/d1ob02349g |pmid=35129563 |s2cid=246418140 |issn=1477-0520|url-access=subscription }}</ref> can be transformed to thionoesters under metal-catalyzed cross-coupling conditions.