Consider the two molecules below.
A chemical drawing software that I won't name says that the one on the left is chiral with configuration R at sulphur, whereas the one on the right isn't.
I checked this with the software developers, and their answer was "Sulfur atoms with three single bonds are not perceived as having stable tetrahedral stereo".
I suspect what they actually meant was that the molecule on the right could be seen as a sulphur with 4 bonds, like:
which is obviously not possible when O is alkylated.
Still, this topic came up because I found an O-akylated sulphoxide similar to the one above in our corporate database (I cannot disclose the exact molecule for confidentiality reasons).
So, if such a molecule can exist, and its registrars thought it appropriate to use a wedge to mark it as a specific enantiomer, what can I conclude?
Can such a sulphoxide have stable stereochemistry, unlike the software developers claimed, or were the registrars wrong, i.e. there is no possible stereochemistry, and they should have used a plain bond?