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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 22, Number 5
JKCSEZ 22(5)
October 20, 1978 

 
Title
Studies on Aromatic Dihydrazines (Ⅳ). A New Synthesis of m-Phenylenedihydrazine via Tetrazonium Salt

방향족 디히드라진에 관한 연구 (제4보). 테트라아조늄염을 통한 메타페닐렌디히드라진의 새 합성법
Author
Woo Young Lee

이우영
Keywords
Abstract
Tetrazonium 염을 거쳐서 m-phenylenedihydrazine (MPDH)을 합성할 수 있었다. 즉, m-phenylenediamine을 진한 염산의 매질 속에서 -10∼-5℃로 유지하고아질산나트륨으로 테트라 아조화한 다음, 이때 생긴 tetrazonium 염을 염화주석(Ⅱ)으로 환원시켜 MPDH를 염산염의 꼴로 얻어 알코올에서 재결정 할 수 있었다. MPDH의 유리염기는 불안정하기 때문에 공기 중에서는 안정한 상태로 얻기 어려우며, 그 염산염은 명확한 녹는 점을 가지지 않고 185℃에서 분해하였다. MPDH도 방향족 monohydrazine의 경우 처럼 mono 또는 dicarbnyl 화합물과 쉽게 축합반응을 일으켜서 dihydrazone 또는 고리모양 화합물을 생성하였다. MPDH와 carbonyl 화합물과의 반응에서 얻은 여러가지 화합물의 구조를 결정하였다.

m-Phenylenedihydrazine(MPDH) was prepared via tetrazonium salt: m-Phenylenediamine was tetrazotized with sodium nitrite at -10∼-5℃ in concentrated hydrochloric acid medium, reused tetrazonium salt was reduced with stannous chloride and MPDH was separated as dihydrochloride which was recrystallized from alcohol. The free base of MPDH being unstable it could hardly be obtained in the air. MPDH·2HCl did not show sharp melting point but decomposed at 185℃. MPDH, like aromatic monohydrazines, condensed with mono-and dicarbonyl compounds giving dihydrazones or cyclic compounds. The structures of condensation products obtained from the reaction of MPDH with carbonyl compounds are determined.

Page
326 - 333
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