Nitrogen inversion process in some camphor-based isoxazolidines

被引：0

作者：

Ali, Shaikh A. ^{[1
]}

Wazeer, Mohamed I. M. ^{[1
]}

Fettouhi, Mohammed B. ^{[1
]}

Iman, Muhammad Z. N. ^{[1
]}

机构：

[1] King Fahd Univ Petr & Minerals, Dept Chem, Dhahran 31261, Saudi Arabia

来源：

ARKIVOC | 2008年

关键词：

Isoxazoldines; nitrogen inversion; invertomers; inversion barriers;

D O I：

10.3998/ark.5550190.0009.g24

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of isoxazolidines has been prepared via asymmetric nitrone cycloaddition reactions of a camphor-based methylenenitrone with several alkenes. The H-1 NMR spectra of the N(2) and C(5)-disubstituted isoxazolidines in CDCl3 at low temperatures revealed the predominant or exclusive presence of the diasteromer having trans disposition of the substituents. The presence of hydroxyl substituent on the camphor moiety permits H-bonding with the N or O of the isoxazolidine ring. The effect of H-bonding - intramolecular in CDCl3 and intermolecular in CD3OD - on the population ratio of the invertomers and nitrogen inversion process has been investigated. The nitrogen inversion barriers are determined using complete line-shape analysis, and their dependence on solvent is discussed.

引用

页码：255 / 267

页数：13

共 50 条

[21] Oxidative Esterification of Aldehydes and Alcohols Catalyzed by Camphor-Based Imidazolium Salts
Bian, Tiancen
Feng, Li
Li, Danfeng
Huang, Jiaxin
Zhao, Yuxun
Xu, Xu
Yang, Yigin
Wang, Shifa
CATALYSIS LETTERS, 2020, 150 (06) : 1812 - 1820
[22] Highly diastereoselective aldol reactions with camphor-based acetate enolate equivalents
Palomo, C
Oiarbide, M
Aizpurua, JM
González, A
García, JM
Landa, G
Odriozola, I
Linden, A
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (22): : 8193 - 8200
[23] Oxidative Esterification of Aldehydes and Alcohols Catalyzed by Camphor-Based Imidazolium Salts
Tiancen Bian
Li Feng
Danfeng Li
Jiaxin Huang
Yuxun Zhao
Xu Xu
Yiqin Yang
Shifa Wang
Catalysis Letters, 2020, 150 : 1812 - 1820
[24] Novel camphor-based amino alcohols and diols for selected asymmetric synthesis
Olubanwo, Olusegun B.
Golen, James A.
Nevalainen, Vesa
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 240
[25] SYNTHESIS OF (+)-CAMPHOR-BASED SULFINIMINES AND THEIR UTILITY IN ASYMMETRIC SYNTHESIS OF AMINE DERIVATIVES
厦门大学学报(自然科学版), 1999, (S1) : 229 - 229
[26] Camphor-based oxazaphospholanes as chiral templates for the enantioselective synthesis of α-chlorophosphonic acids
Giovenzana, GB
Pagliarin, R
Palmisano, G
Pilati, T
Sisti, M
TETRAHEDRON-ASYMMETRY, 1999, 10 (22) : 4277 - 4280
[27] Efficient synthesis of camphor-based polycarbonates: a direct route to recyclable polymers
Jiang, Bo
Thomas, Christophe M. M.
CATALYSIS SCIENCE & TECHNOLOGY, 2023, 13 (13) : 3910 - 3915
[28] Metronidazole-Loaded Camphor-Based In Situ Forming Matrix for Periodontitis Treatment
Kritamorn Jitrangsri
Nutdanai Lertsuphotvanit
Ngamsil Kabthong
Thawatchai Phaechamud
AAPS PharmSciTech, 24
[29] Switch in asymmetric induction sense in cycloadditions using camphor-based nitroso dienophiles
Wang, YC
Lu, TM
Elango, S
Lin, CK
Tsai, CT
Yan, TH
TETRAHEDRON-ASYMMETRY, 2002, 13 (07) : 691 - 695
[30] Synthesis of D-(+)-camphor-based N-acylhydrazones and their antiviral activity
Kovaleva, Kseniya S.
Zubkov, Fedor I.
Bormotov, Nikolay I.
Novikov, Roman A.
Dorovatovskii, Pavel V.
Khrustalev, Victor N.
Gatilov, Yuriy V.
Zarubaev, Vladimir V.
Yarovaya, Olga I.
Shishkina, Larisa N.
Salakhutdinov, Nariman F.
MEDCHEMCOMM, 2018, 9 (12) : 2072 - 2082

← 1 2 3 4 5 →