S N (ANRORC) mechanism XX. Degenerate ring transformations in reactions of 1,2,4,5‐tetrazines with hydrazine | Zendy

CounottePotman A. D. | Zendy; van der Plas H. C. | Zendy

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S N (ANRORC) mechanism XX. Degenerate ring transformations in reactions of 1,2,4,5‐tetrazines with hydrazine

Author(s) -

CounottePotman A. D.,

van der Plas H. C.

Publication year - 1978

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570150316

Subject(s) - chemistry , hydrazine (antidepressant) , ring (chemistry) , tetrazine , degenerate energy levels , medicinal chemistry , deamination , mechanism (biology) , mass spectrometry , computational chemistry , organic chemistry , chromatography , philosophy , physics , epistemology , quantum mechanics , enzyme

Evidence is presented that the hydrazinolysis of 3‐amino‐ (5) and 3‐bromo‐6‐methyl‐1,2,4,5‐tetrazine ( 7 ) into the 3‐hydrazino‐6‐methyl‐1,2,4,5‐tetrazine ( 6* ) with 15 N‐labelled hydrazine leads to incorporation of 15 N in the 1,2,4,5‐tetrazine ring. Thus in the hydrazino‐deamination and hydrazino‐debromination a S N (ANRORC) mechanism is operative. Based on quantitative mass spectrometry it was found that 20‐25% of both 5 and 7 reacts according to this S N ‐(ANRORC) mechanism. The mechanism of these degenerate ring transformations is discussed.

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