SNi
In
A typical representative
Thionyl chloride first reacts with the alcohol to form an alkyl chloro sulfite, actually forming an intimate ion pair. The second step is the concerted loss of a sulfur dioxide molecule and its replacement by the chloride, which was attached to the sulphite group. The difference between SN1 and SNi is actually that the ion pair is not completely dissociated, and therefore no real carbocation is formed, which else would lead to a racemisation.
This reaction type is linked to many forms of
This reaction mechanism is supported by the observation that addition of pyridine to the reaction leads to inversion. The reasoning behind this finding is that pyridine reacts with the intermediate sulfite replacing chlorine. The dislodged chlorine has to resort to nucleophilic attack from the rear as in a regular nucleophilic substitution.[3]
In the complete picture for this reaction the sulfite reacts with a chlorine ion in a standard
See also
References
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- ISBN 9780470084946.