N-Carbonylsulfamoyl chloride (NCSA) is an intermediate that can be obtained from cyanogen chloride and sulfur trioxide, and which reacts with many compounds, via electrophilic substitution, much more readily than other isocyanates. Reactions with compounds containing hydroxyl, amino, or carboxyl groups lead to N-chlorosulfonylurethanes, -meas, and -amides, respectively. This group of products also includes the parent substance sulfamoyl chloride (arnidosulfonyl chloride). The reaction of N-carbonylsulfamoyl chloride with olefins provides an easy route, not only to derivatives of @-amino acids and unsaturated carboxylic acids, but also to many @-lactams New, very reactive sulfonylisocyanates of several types can be obtained by further reactions of primary products obtained from N-carbonylsulfamoyl chloride and by the reaction of N-carbonylsulfamoyl chloride with olefins in the presence of free-radical formers. When allowed to react with a number of compounds, NCSA undergoes loss of carbon dioxide to form products containing the grouping = N-SO2CI.
β‐Lactams can be prepared by cyclization of β‐aimno acid esters. Recently they have become available also from olefins by addition of N‐carbonysulfamyl chloride (isocyanatosulfonyl chloride) and from aldehydes by reaction with N‐carbonylsulfamyl chloride and ketene. Condensative or anionic polymerization results in polyamides the chains of which contain many more amide groups than the chains of polyamides of the nylon‐6 type. Hence the new polymers resemble silk moreclosely. Fibers and films can be prepared from solution.
Die Umsetzungvon N-Carbonyl-sulfamidsaurechlorid O = C = N -SOzCl (NCSA) mit gewissen Olefinen fiihrt zu P-Lactam-N-sulfochloriden und (oder) ungesattigten Carbonsaureamjd-N-sulfochloriden. Dieser Reaktionsweg erschlieDt, ausgehend von einfachen Ausgangsstoffen, viele Derivate von P-Aminocarbonsauren und ungesattigten Carbonsauren. Einjge rnit NCSA reagierende Ringsysteme ergeben primar Verbindungen -$-CO-NH-S02CI. -Die zu (3-Lactamen rnit unsubstituierter NH-Gruppe fiihrenden, auch in technischem MaBstabe gangbaren Wege, erschlieDen mannigfaltige praparative MBglichkeiten. -SchlieDlich wird eine weitere Reaktionsfolge beschrieben, die, ausgehend von Aldehyden unter Verwendung von NCSA und Ketenen, ebenfalls zu @-Lactamen fiihrt.
Bei der Einwirkung von Schwefeltrioxyd auf Chlorcyan entstehen die bisher nicht beschriebenen Verbindungen CO3NClS, CO6NClS2 und C2O3N2Cl2S, deren Konstitution sichergestellt wird. Es werden Vorschriften zur laboratoriumsmäßigen Herstellung dieser Verbindungen mitgeteilt und deren Eigenschaften näher beschrieben.
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