Reaction of 3,3,3-Tribromo- and 1,3,3,3-Tetrabromo-1-nitroprop-1-enes with Aliphatic Dienes

The First Examples of [3+2] Cycloadditions with the Participation of (E)-3,3,3-Tribromo-1-Nitroprop-1-Ene

“…In particular, Z-C -aryl- N -phenylnitrones ( 1a–g ) were prepared via condensation between N -phenylohydroxylamine and respective arylaldehydes [ 31 ]. The 3,3,3-bromo-1-nitroprop-1-ene ( 2 ) was obtained via three-step method, starting from nitromethane and bromal (see Supplementary Material for the details) [ 17 , 18 ]. Commercially available (Sigma Aldrich, St. Louis, MO, USA) chemicals have been used as solvents and components for the further synthesis of addends for considered 32CA.…”

“…Regarding 3,3,3-trifluor-1-nitroprop-1-ene, many interesting scientific works are also available at the present time [ 4 , 5 , 6 , 15 , 16 ]. In contrast, only some incidential contributions regarding the physicochemistry of 3,3,3-tribromo-1-nitroprop-1-ene (TBMN) are available [ 17 , 18 ]. In particular, only one simple example of [4+2] cycloaddition with the participation of TBMN and simple aliphatic dienes is known [ 17 ].…”

“…In contrast, only some incidential contributions regarding the physicochemistry of 3,3,3-tribromo-1-nitroprop-1-ene (TBMN) are available [ 17 , 18 ]. In particular, only one simple example of [4+2] cycloaddition with the participation of TBMN and simple aliphatic dienes is known [ 17 ]. Any other examples of 32CAs of TBMN were not described for this time.…”