Synthesis of C-Unsubstituted 1,2-Diazetidines and Their Ring-Opening Reactions via Selective N-N Bond Cleavage

被引：11

作者：

Lakmal, Hetti Handi Chaminda ^{[1
]}

Xu, Joanna Xiuzhu ^{[1
]}

Xu, Xue ^{[1
]}

Ahmed, Bassem ^{[2
]}

Fong, Christopher ^{[2
]}

Szalda, David J. ^{[2
]}

Ramig, Keith ^{[2
]}

Sygula, Andrzej ^{[1
]}

Webster, Charles Edwin ^{[1
]}

Zhang, Dongmao ^{[1
]}

Cui, Xin ^{[1
]}

机构：

[1] Mississippi State Univ, Dept Chem, Mississippi State, MS 39762 USA

[2] CUNY, Baruch Coll, Dept Nat Sci, 17 Lexington Ave, New York, NY 10010 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 16期

基金：

美国国家科学基金会;

关键词：

MOLECULAR CALCULATIONS; BASIS-SETS; POLARIZATION; HYDRAZINES; CHEMISTRY; ATOMS; WATER;

D O I：

10.1021/acs.joc.8b01223

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

C-Unsubstituted 1,2-diazetidines, a rarely studied type of four-membered heterocyclic compounds, were synthesized through an operationally simple intermolecular vicinal disubstitution reaction. 1,2-Diazetidine derivatives bearing various N-arylsulfonyl groups were readily accessed and studied by experimental and computed Raman spectra. The ring-opening reaction of the diazetidine was explored and resulted in the identification of a selective N-N bond cleavage with thiols as nucleophiles, which stereoselectively produced a new class of N-sulfenylimine derivatives with C-aminomethyl groups.

引用

页码：9497 / 9503

页数：7

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