Depolymerizable poly(benzyl ether)-based materials for selective room temperature recycling

2015 ◽  
Vol 17 (9) ◽  
pp. 4541-4545 ◽  
Author(s):  
Matthew S. Baker ◽  
Hyungwoo Kim ◽  
Michael G. Olah ◽  
Gregory G. Lewis ◽  
Scott T. Phillips
Keyword(s):  
Room Temperature ◽  
Quinone Methide ◽  
Benzyl Ether ◽  
Temperature Separation ◽  
Benzyl Ethers

Straightforward modifications to quinone methide monomers creates self-immolative poly(benzyl ethers) that enable room temperature separation and recycling of plastics.

Metal-free synthesis of 1H-isochromenes via benzyl ether-assisted, electrophilic addition of diaryl acetylenes

2021 ◽  
Author(s):  
Tzu-Hsuan Kuan ◽  
Trimurtulu Kotipalli ◽  
Cheng-Chun Chen ◽  
Duen-Ren Hou
Keyword(s):  
Intramolecular Cyclization ◽  
Room Temperature ◽  
Electrophilic Addition ◽  
Benzyl Ether ◽  
Metal Free ◽  
Benzyl Ethers ◽  
The Stability ◽  
Diaryl Acetylenes

Bromotrimethylsilane (TMSBr) promoted, intramolecular cyclization of (o-arylethynyl)benzyl ethers to form 1H-isochromenes at room temperature is reported. Further studies indicated that the stability of vinyl carbocations is crucial, similar to the...

scholarly journals Removal of benzylidene acetal and benzyl ether in carbohydrate derivatives using triethylsilane and Pd/C

2013 ◽  
Vol 9 ◽  
pp. 74-78 ◽  
Author(s):  
Abhishek Santra ◽  
Tamashree Ghosh ◽  
Anup Kumar Misra
Keyword(s):  
Room Temperature ◽  
Transfer Hydrogenation ◽  
Benzyl Ether ◽  
Catalytic Transfer Hydrogenation ◽  
Excellent Yield ◽  
Benzyl Ethers ◽  
Catalytic Transfer

Clean deprotection of carbohydrate derivatives containing benzylidene acetals and benzyl ethers was achieved under catalytic transfer hydrogenation conditions by using a combination of triethylsilane and 10% Pd/C in CH3OH at room temperature. A variety of carbohydrate diol derivatives were prepared from their benzylidene derivatives in excellent yield.

Visible Light-Mediated Oxidative Debenzylation

2020 ◽  
Author(s):  
Cristian Cavedon ◽  
Eric T. Sletten ◽  
Amiera Madani ◽  
Olaf Niemeyer ◽  
Peter H. Seeberger ◽  
...  
Keyword(s):  
Reaction Time ◽  
Visible Light ◽  
Functional Groups ◽  
Continuous Flow ◽  
Protecting Groups ◽  
Benzyl Ether ◽  
Complex Molecules ◽  
Protective Groups ◽  
Benzyl Ethers ◽  
Harsh Conditions

Protecting groups are key in the synthesis of complex molecules such as carbohydrates to distinguish functional groups of similar reactivity. The harsh conditions required to cleave stable benzyl ether protective groups are not compatible with many other protective and functional groups. The mild, visible light-mediated debenzylation disclosed here renders benzyl ethers orthogonal protective groups. Key to success is the use of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as stoichiometric or catalytic photooxidant such that benzyl ethers can be cleaved in the presence of azides, alkenes, and alkynes. The reaction time for this transformation can be reduced from hours to minutes in continuous flow. <br>

A Facile, Efficient and Selective Deprotection of P - Methoxy Benzyl Ethers Using Zinc (II) Trifluoromethanesulfonate

2019 ◽  
Vol 16 (12) ◽  
pp. 955-958
Author(s):  
Reddymasu Sireesha ◽  
Reddymasu Sreenivasulu ◽  
Choragudi Chandrasekhar ◽  
Mannam Subba Rao
Keyword(s):  
Room Temperature ◽  
Protecting Groups ◽  
Side Reactions ◽  
Reaction Conditions ◽  
Acid Sensitivity ◽  
Time Period ◽  
Protective Groups ◽  
Benzyl Ethers ◽  
Last Stage ◽  
Zinc Triflate

: Deprotection is significant and conducted over mild reaction conditions, in order to restrict any more side reactions with sensitive functional groups as well as racemization or epimerization of stereo center because the protective groups are often cleaved at last stage in the synthesis. P - Methoxy benzyl (PMB) ether appears unique due to its easy introduction and removal than the other benzyl ether protecting groups. A facile, efficient and highly selective cleavage of P - methoxy benzyl ethers was reported by using 20 mole% Zinc (II) Trifluoromethanesulfonate at room temperature in acetonitrile solvent over 15-120 min. time period. To study the generality of this methodology, several PMB ethers were prepared from a variety of substrates having different protecting groups and subjected to deprotection of PMB ethers using Zn(OTf)2 in acetonitrile. In this methodology, zinc triflate cleaves only PMB ethers without affecting acid sensitivity, base sensitivity and also chiral epoxide groups.

A versatile iodo(iii)etherification of terminal ethynylsilanes using BF3–OiPr2 and alkyl benzyl ethers

2021 ◽  
Author(s):  
Takuya Matsumoto ◽  
Hiroshi Hagiyama ◽  
Kanetsugu Kuribayashi ◽  
Kazuhito Hioki ◽  
Hikaru Fujita ◽  
...  
Keyword(s):  
Benzyl Ether ◽  
Alkoxyl Group ◽  
Group Transfer ◽  
Benzyl Ethers

BF3–OiPr2 and alkyl benzyl ether combining system enables a chemoselective alkoxyl group transfer in the synthesis of (E)-α-silyl-β-alkoxyvinyl-λ3-iodanes.

Nitric‐Acid‐Catalyzed Aerobic Conversion of Benzyl Ethers to Benzaldehydes at Room Temperature

2020 ◽  
Vol 5 (45) ◽  
pp. 14288-14291
Author(s):  
Zhenpeng Shen ◽  
Zhe Zhao ◽  
Yun‐Lai Ren ◽  
Wenbo Liu ◽  
Xinzhe Tian ◽  
...  
Keyword(s):  
Nitric Acid ◽  
Room Temperature ◽  
Benzyl Ethers ◽  
Acid Catalyzed

scholarly journals Visible-light unmasking of heterocyclic quinone methide radicals from alkoxyamines

2019 ◽  
Vol 55 (97) ◽  
pp. 14665-14668 ◽  
Author(s):  
Patrick Kielty ◽  
Pau Farràs ◽  
Patrick McArdle ◽  
Dennis A. Smith ◽  
Fawaz Aldabbagh
Keyword(s):  
Visible Light ◽  
Room Temperature ◽  
Quinone Methide ◽  
Heterocyclic Quinone

Controllable room-temperature visible-light activated nitroxide (TEMPO)-release from benzimidazolequinone alkoxyamines and bis-alkoxyamines.

Catalyst-Free Room-Temperature Self-Healing Polymer Networks Based on Dynamic Covalent Quinone Methide-Secondary Amine Chemistry

2021 ◽  
Author(s):  
Yuanxing Zhang ◽  
Ying Wu ◽  
Jiayi Li ◽  
Ke Zhang
Keyword(s):  
Secondary Amine ◽  
Michael Addition ◽  
Room Temperature ◽  
Polymer Networks ◽  
Quinone Methide ◽  
Self Healing ◽  
Ambient Conditions ◽  
Catalyst Free ◽  
External Stimuli

An aza-Michael addition between 2,6-di-t-butyl-7-phenyl-p-quinone methide and secondary amine was demonstrated to hold the dynamic covalent reaction property under ambient conditions requiring no external stimuli. Based on this dynamic covalent...

Sign in / Sign up

Export Citation Format

Share Document