Nitrosoureas hydrolysis

Major sources are the basic hydrolysis of V-methyl-V-nitrosourea (or V-methyl-V-nitroso-/)-toluenesulfonamide (Diazald ) or l-methyl-3-nitro-l-nitrosoguanidine (MNNG). 

The NH acidities of some sterically hindered ureas, namely the ureido esters (93), have been reported.81 The kinetics and mechanism of the alkaline hydrolysis of urea and sodium cyanate, NaCNO, have been studied at a number of temperatures.82 Urea hydrolysis follows an irreversible first-order consecutive reaction path. Tetrahedral intermediates are not involved and an elimination-addition mechanism operates. Sodium cyanate follows irreversible pseudo-first-order kinetics. The decomposition of the carcinogen /V-mcthyl-/V-nitrosourea (19) was dealt with earlier.19 The pyrolysis of (V-acetylurea goes by a unimolecular first-order elimination reaction.83... 

Reactions of aminocyclopropanes are discussed extensively in Chapter 22 of this book, therefore only some unusual aminocyclopropanes will be treated here. One example is cyclopropyl isocyanide which after deprotonation, reaction with carbonyl compounds, and hydrolysis can be transformed to cyclobutanones (equation 60) , thereby taking advantage of the acidifying effect of the isocyanide function. 7-Norcarane nitrosourea is the key starting material in Jendralla and Spur s approach to rrans-cycloheptene adducts (equation 61) ... 

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