Abstract
Five-membered cyclic sulfamidates are very valuable electrophiles in organic synthesis and readily used on a multikilogram scale.However,their thermal degradation is underreported and might lead to unforeseen and undesirable safety events.In addition,ring or nitrogen substitution can have a tremendous influence on cyclic sulfamidate reactivity toward bases and therefore impact the overall safety assessment of a process.An understanding of such behavior is therefore of high importance in the industry while designing a synthetic route,as a change of,e.g.,a protecting group can increase the thermal safety of a step on scale.We report herein the thermal degradation investigation as well as the structure-related reactivity exploration of cyclic sulfamidates,including their use in combination with strong bases.The design of a predictive model to rapidly assess the thermal hazard based on collected data and selected molecular descriptors is also presented.
NSTL