Zwitterions as Intermediates of the 1,3‐Dipolar Cycloaddition of Electrophilic Azides to 5‐Alkylidenedihydrotetrazoles – the Other Non‐Concerted Limiting Case | Zendy

Quast Helmut | Zendy; Regnat Dieter | Zendy; Peters EvaMaria | Zendy; Peters Karl | Zendy; von Schnering Hans Georg | Zendy

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Zwitterions as Intermediates of the 1,3‐Dipolar Cycloaddition of Electrophilic Azides to 5‐Alkylidenedihydrotetrazoles – the Other Non‐Concerted Limiting Case

Author(s) -

Quast Helmut,

Regnat Dieter,

Peters EvaMaria,

Peters Karl,

von Schnering Hans Georg

Publication year - 1990

Publication title -

angewandte chemie international edition in english

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 0570-0833

DOI - 10.1002/anie.199006951

Subject(s) - cycloaddition , steric effects , chemistry , electrophile , zwitterion , limiting , ring (chemistry) , computational chemistry , photochemistry , stereochemistry , medicinal chemistry , molecule , organic chemistry , catalysis , mechanical engineering , engineering

The isolable zwitterions 2 and the tetrahydrotetrazines 3 are formed in the 1,3 ‐dipolar cycloadditions of R 3 N 3 to 1 . It has been established X‐ray crystallo‐graphically that a strong steric hindrance is responsible for ring closure between the very close centers of opposite charge being difficult in 2 (R 1 = H, R 2 = t Bu = Mes). A detailed investigation of the reactions clearly confirms that the zwitterions 2 are actually the intermediates of a non‐concerted cycloaddition (R 1 = H. Me; R 2 = Me, t Bu; R 3 = (NO 2 ) 3 C 6 H 2 , p ‐Tos, Mes).

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