The impact of Lewis acid variation on reactions with di-tert-butyl diazo diesters

被引：1

作者：

Bedi, Vaibhav ^{[1
]}

Mandal, Dipendu ^{[1
,2
]}

Hussain, Zahid ^{[2
]}

Chen, Shi-Ming ^{[1
]}

Wu, Yile ^{[2
]}

Qu, Zheng-Wang ^{[3
]}

Grimme, Stefan ^{[3
]}

Stephan, Douglas W. ^{[1
,2
]}

机构：

[1] Univ Toronto, Dept Chem, 80 St George St, Toronto, ON M5S 3H6, Canada

[2] Ningbo Univ, Inst Drug Discovery Technol, Ningbo 315211, Zhejiang, Peoples R China

[3] Rhein Friedrich Wilhelms Univ Bonn, Clausius Inst Phys & Theoret Chem, Mulliken Ctr Theoret Chem, Beringstr 4, D-53115 Bonn, Germany

来源：

DALTON TRANSACTIONS | 2024年 / 53卷 / 02期

基金：

加拿大自然科学与工程研究理事会;

关键词：

BASIS-SETS; DENSITY; CAPTURE; REDUCTION; CHEMISTRY; ACCURATE; NITROGEN; DESIGN; COSMO; BOND;

D O I：

10.1039/d3dt03506a

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Reactions of (tBuO(2)CN)(2) with Lewis acids and FLPs have previously been shown to prompt the formation of diazene compounds. In this work, we show that the reaction of (tBuO(2)CN)(2) with 9-BBN leads to a bicyclic heterocyclic product (tBuOCO(BBN)CN)(2) 1. In contrast, the reactions of (tBuO(2)CN)(2) with BF3 or [Et3Si][B(C6F5)(4)] lead to the isolation of [tBuNHNH(2)tBu][BF4] 2 and [tBuN(H)NtBu][B(C6F5)(4)] 3, respectively. The mechanism for the formation of 2 is probed computationally, demonstrating that steric and electronic considerations of the Lewis acid impact the reaction pathway.

引用

页码：439 / 443

页数：5

共 50 条

[21] DIAZO TRANSFER BY MEANS OF PHASE-TRANSFER CATALYSIS - DI-TERT-BUTYL DIAZOMALONATE
LEDON, HJ
ORGANIC SYNTHESES, 1988, 50-9 : 414 - 417
[22] THE PHOTOLYSIS OF DI-TERT-BUTYL PEROXIDE
FREY, HM
PROCEEDINGS OF THE CHEMICAL SOCIETY OF LONDON, 1959, (12): : 385 - 386
[23] PHOTOLYSIS OF DI-TERT-BUTYL PEROXIDE-AZOMETHANE AND DI-TERT-BUTYL PEROXIDE-ISOBUTANE MIXTURES
MCMILLAN, GR
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (10) : 2422 - 2425
[24] PHOTOLYSIS OF DI-TERT-BUTYL PEROXIDE UNDER ACID CONDITIONS
COOKSON, PG
DAVIES, AG
ROBERTS, BP
TSE, MW
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (22) : 937 - 938
[25] PREPARATION OF TERT-BUTYLMALEIC ACID AND ITS DI-TERT-BUTYL ESTER
JENSEN, SR
MUNCHPET.J
ACTA CHEMICA SCANDINAVICA, 1967, 21 (07): : 1963 - &
[26] Development of Efficient Processes for the Preparation of Di-tert-butyl Potassium Phosphate and Di-tert-butyl (Chloromethyl) Phosphate
Zheng, Bin
Fox, Richard J.
Sugiyama, Masano
Fritz, Alan
Eastgate, Martin D.
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2014, 18 (05) : 636 - 642
[27] Alcohols and di-tert-butyl dicarbonate:: How the nature of the Lewis acid catalyst may address the reaction to the synthesis of tert-butyl ethers
Bartoli, Giuseppe
Bosco, Marcella
Carlone, Armando
Dalpozzo, Renato
Locatelli, Manuela
Melchiorre, Paolo
Sambri, Letizia
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (26): : 9580 - 9588
[28] THE PREPARATION OF DI-TERT-BUTYL CARBONATE AND TERT-BUTYL CHLOROCARBONATE
CHOPPIN, AR
ROGERS, JW
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1948, 70 (09) : 2967 - 2967
[29] Di-tert-butyl Phosphate Complexes of Titanium
Lugmair, C. G.
Tilley, T. D.
Inorganic Chemistry, 37 (08):
[30] A NOTE ON PREPARATION OF DI-TERT-BUTYL ACETAL
JANSSON, I
SUOMEN KEMISTILEHTI, 1965, B 38 (10): : 222 - &

← 1 2 3 4 5 →