Synthesis and Wittig Rearrangement of 3-and 4-Benzyloxyphenylphosphonamidates

被引：4

作者：

Aitken, R. Alan ^{[1
]}

Inwood, Ryan A. ^{[1
]}

机构：

[1] Univ St Andrews, EaStCHEM Sch Chem, St Andrews KY16 9ST, Fife, Scotland

来源：

ORGANICS | 2023年 / 4卷 / 01期

基金：

英国工程与自然科学研究理事会;

关键词：

Wittig rearrangement; phosphonamidate; diarylmethanol; aryl benzyl ether;

D O I：

10.3390/org4010005

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of seven O-ethyl-N-butylphenylphosphonamidates with benzyl ether substituents at the para or meta position have been prepared and fully characterised. Upon treatment with n-butyllithium in THF at RT, these undergo Wittig rearrangement in six cases to give the novel phosphonamidate-substituted diarylmethanols in moderate to good yield.

引用

页码：59 / 69

页数：11

共 15 条

[1] Further Studies on the [1,2]-Wittig Rearrangement of 2-(2-Benzyloxy)aryloxazolines [J].

Aitken, R. Alan ;

Harper, Andrew D. ;

Inwood, Ryan A. .

MOLECULES, 2022, 27 (10)

[2] Access to Diarylmethanols by Wittig Rearrangement ofortho-,meta-, andpara-Benzyloxy-N-Butylbenzamides [J].

Aitken, R. Alan ;

Harper, Andrew D. ;

Inwood, Ryan A. ;

Slawin, Alexandra M. Z. .

JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (07) :4692-4701

[3] Rationalisation of Patterns of Competing Reactivity by X-ray Structure Determination: Reaction of Isomeric (Benzyloxythienyl)oxazolines with a Base [J].

Aitken, R. Alan ;

Harper, Andrew D. ;

Slawin, Alexandra M. Z. .

MOLECULES, 2021, 26 (24)

[4] Base-Induced Cyclisation of ortho -Substituted 2-Phenyloxazolines to Give 3-Aminobenzofurans and Related Heterocycles [J].

Aitken, R. Alan ;

Harper, Andrew D. ;

Slawin, Alexandra M. Z. .

SYNLETT, 2017, 28 (14) :1738-1742

[5] Structurally Divergent Lithium Catalyzed Friedel-Crafts Reactions on Oxetan-3-ols: Synthesis of 3,3-Diaryloxetanes and 2,3-Dihydrobenzofurans [J].

Croft, Rosemary A. ;

Mousseau, James J. ;

Choi, Chulho ;

Bull, James A. .

CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (45) :16271-16276

[6] SYNTHESIS AND NMR SPECTROSCOPIC INVESTIGATION OF PHENYLPHOSPHORYL DERIVATIVES [J].

DUDDECK, H ;

LECHT, R .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1987, 29 (2-4) :169-178

[7]

Firooznia F., 2010, PCT International Patent Application, Patent No. [WO201005506 A1, 201005506]

[8] Bromo derivatives of benzylphenols I Some monobromo, dibromo and tribromo derivatives of ortho and para benzylphenols [J].

Huston, RC ;

Neeley, A ;

Fayerweather, BL ;

D'Arcy, HM ;

Maxfield, FH ;

Ballard, MM ;

Lewis, WC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1933, 55 :2146-2149

[9] Synthesis of cage-type molecules with π-cavity and selective gas-phase cation complexation [J].

Kim, J ;

Kim, YK ;

Park, N ;

Hahn, JH ;

Ahn, KH .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (18) :7087-7092

[10] Concerning the carbinol rearrangement from benzyl ether (I.). [J].

Schorigin, P .

BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1924, 57 :1634-1637

← 1 2 →