cis (Z) jasmone

.

 cis (Z) jasmone 

(Can. J. Chem. 1978, Vol 56, p2301)

e.g. How might we attempt to make Z jasmone – an important constituent of many perfumes?

In fact one synthesis uses the following as carbon sources:

It is not clear from this however, how the chemistry might be done!  Therefore just being given the starting materials is not sufficient to help plan a synthesis.
Note the importance of CCBFR.

We need a logical planning method.

Retrosynthetic Analysis (The Disconnection Approach)

Originated by E.J. Corey (Nobel Prize 1990)               p169 – 172

                                                                                    p259 – 260

                                                                                    p354 – 359

Interesting compound, Spoked-wheel macrocycles

.

 

• Chemical Formula: C₇₇₄H₉₉₆N₁₈O₃₆Si₁₂
• Molecular Weight: 11465.32
• Elemental Analysis: C, 81.08; H, 8.76; N, 2.20; O, 5.02; Si, 2.94

 4-({2-[4-(2-{9-[4-(4-{2-[2,5-Bis(octyloxy)-4-(2-{4-[pentakis({4-[2-(4-{2-[4-(4-{2,7-bis[2-(4-{2-[(3-cyanopropyl)bis(propan-2-yl)silyl]ethynyl}-2,5-bis(octyloxy)phenyl)ethynyl]-9H-carbazol-9-yl}phenyl)phenyl]ethynyl}-2,5-bis(octyloxy)phenyl)ethynyl]phenyl})phenyl]phenyl}ethynyl)phenyl]ethynyl}phenyl)phenyl]-7-[2-(4-{2-[(3-cyanopropyl)bis(propan-2-yl)silyl]ethynyl}-2,5-bis(octyloxy)phenyl)ethynyl]-9H-carbazol-2-yl}ethynyl)-2,5-bis(octyloxy)phenyl]ethynyl}bis(propan-2-yl)silyl)butanenitrile

Compound 7

From Fluctuating exciton localization in giant π-conjugated spoked-wheel macrocycles

• A. Vikas Aggarwal,
• Alexander Thiessen,
• Alissa Idelson,
• Daniel Kalle,
• Dominik Würsch,
• Thomas Stangl,
• Florian Steiner,
• Stefan-S. Jester,
• Jan Vogelsang,
• Sigurd Höger
• & John M. Lupton

Nature Chemistry5,964–970(2013)

doi:10.1038/nchem.1758

Supplementary Information

 

C774H996N18O36Si12
Name compound: 4-({2-[4-(2-{9-[4-(4-{2-[2,5-Bis(octyloxy)-4-(2-{4-[pentakis({4-[2-(4-{2-[4-(4-{2,7-bis[2-(4-{2-[(3-cyanopropyl)bis(propan-2-yl)silyl]ethynyl}-2,5-bis(octyloxy)phenyl)ethynyl]-9H-carbazol-9-yl}phenyl)phenyl]ethynyl}-2,5-bis(octyloxy)phenyl)ethynyl]phenyl})phenyl]phenyl}ethynyl)phenyl]ethynyl}phenyl)phenyl]-7-[2-(4-{2-[(3-cyanopropyl)bis(propan-2-yl)silyl]ethynyl}-2,5-bis(octyloxy)phenyl)ethynyl]-9H-carbazol-2-yl}ethynyl)-2,5-bis(octyloxy)phenyl]ethynyl}bis(propan-2-yl)silyl)butanenitrile.

https://www.instagram.com/p/BBMfA4bBkvZY9QhsJV6ff6khLjUE6F9MqBqRu40/

• Synthetic Procedure: See article for the definitive version of this procedure and for full experimental details.6 (19.0 mg, 14.7 µmol), CuI (3.4 mg, 17.7 µmol), Pd₂dba₃(4.0 mg, 4.4 µmol), and tri(t‑butyl)phosphine (6.0 mg, 29.5 µmol) were mixed in a microwave tube and sealed with a septum. In parallel, a solution of 5 (241.7 mg, 132.6 µmol) in piperidine (2 mL) was purged with argon for 1 h. Then the latter was transferred to the microwave tube and the mixture was heated at 120 °C for 16 min in a microwave instrument (max. power: 300 W). After cooling to r.t., the tube was opened and the reaction mixture was diluted with MTBE. The organic phase was washed with aq. H₂SO₄ (10 %) and brine. It was dried over MgSO₄ and the solvent was removed under reduced pressure. The residue was purified by column chromatography (CH:DCM = 65:35 ‑ 68:32), and 7 (126 mg, 10.9 µmol, 74 %) was obtained as a yellow solid. ¹H NMR (500 MHz, CDCl₃, 298 K) δ [ppm] = 8.09 (d, ³J_H,H = 8.2 Hz, 12 H), 7.87 (d, ³J_H,H = 8.5 Hz, 12 H), 7.76 – 7.60 (m, 48 H), 7.55 – 7.46 (m, 12 H), 7.16 (d, ³J_H,H = 8.0 Hz, 12 H), 7.03 (s, 6 H), 7.02 (s, 6 H), 6.96 (s, 12 H), 6.93 (s, 12 H), 6.86 (d, ³J_H,H = 8.1 Hz, 12 H), 4.10 – 3.99 (m, 48 H), 3.99 – 3.90 (m, 24 H), 2.42 (t, ³J_H,H = 7.0 Hz, 24 H), 1.95 – 1.72 (m, 96 H), 1.62 – 1.16 (m, 360 H), 1.15 – 0.97 (m, 168 H), 0.97 – 0.76 (m, 132 H); ¹H NMR (500 MHz, CD₂Cl₂, 298 K) δ [ppm] = 8.14 (d, ³J_H,H = 8.1 Hz, 12 H), 7.92 (d, ³J_H,H = 8.5 Hz, 12 H), 7.79 – 7.66 (m, 36 H), 7.64 (s, 12 H), 7.54 – 7.44 (m, 12 H), 7.20 (d, ³J_H,H = 8.2 Hz, 12 H), 7.05 (s, 6 H), 7.02 (s, 6 H), 6.99 (s, 12 H), 6.97 – 6.93 (m, 24 H), 4.08 – 3.98 (m, 48 H), 3.98 – 3.92 (m, 24 H), 2.41 (t, ³J_H,H = 7.0 Hz, 24 H), 1.96 – 1.71 (m, 96 H), 1.65 – 1.17 (m, 360 H), 1.17 – 0.99 (m, 168 H), 0.99 – 0.76 (m, 132 H); ¹³C NMR (126 MHz, CDCl₃, 298 K) δ [ppm] = 154.78, 154.06, 153.94, 153.79, 141.60, 140.49, 140.41, 140.10, 136.79, 132.63, 131.73, 130.90, 128.94, 127.99, 127.36, 124.58, 123.55, 123.50, 121.54, 121.26, 120.86, 120.21, 118.04, 117.40, 117.28, 116.51, 114.96, 114.65, 114.07, 113.58, 113.47, 104.31, 96.51, 95.56, 94.91, 87.61, 86.62, 70.16, 70.04, 70.00, 69.56, 32.27, 32.25, 32.24, 32.18, 29.82, 29.79, 29.75, 29.73, 29.71, 29.68, 26.52, 26.42, 26.40, 23.14, 23.13, 23.09, 23.08, 21.70, 21.17, 18.65, 18.41, 14.63, 14.57, 14.52, 14.50, 12.20, 10.04; ¹³C NMR (126 MHz, CD₂Cl₂, 298 K) δ [ppm] = 154.88, 154.20, 154.11, 153.93, 141.87, 140.89, 140.63, 140.50, 140.40, 136.88, 132.68, 132.04, 130.83, 129.11, 128.15, 127.61, 124.49, 123.69, 123.50, 121.66, 121.44, 121.10, 120.32, 117.99, 117.47, 117.28, 116.70, 114.90, 114.62, 114.20, 113.84, 113.62, 104.31, 96.45, 95.91, 95.35, 94.94, 87.71, 86.85, 86.80, 70.22, 70.14, 69.82, 32.44, 32.35, 29.97, 29.93, 29.90, 29.88, 29.83, 29.83, 26.69, 26.67, 26.58, 26.54, 23.31, 23.29, 23.25, 23.24, 21.89, 21.22, 18.56, 18.32, 14.57, 14.50, 14.45, 14.43, 12.35, 10.14;MS (MALDI-TOF, DCTB) (calcd. for C₇₇₄H₉₉₆N₁₈O₃₆Si₁₂ monoisotopic: 11455.39, distr. max.: 11465.32): m/z11965.9 [M+2*DCTB]⁺, 11716.6 [M+DCTB]⁺, 11465.3 [M]⁺, 5856.8 [M+DCTB]²⁺, 5733.5 [M]²⁺; GPC (in THF vs. PS): M_p = 11580 g mol^-1.

Soheil Zabihi
 http://www.nature.com/nchem/journal/v5/n11/compound/nchem.1758_comp7.html
http://www.nature.com/nchem/journal/v5/n11/extref/nchem.1758-s1.pdf
http://www.nature.com/nchem/journal/v5/n11/extref/nchem.1758-s1.pdf

Affiliations

1. Kekulé-Institut für Organische Chemie und Biochemie der Universität Bonn, Gerhard-Domagk-Strasse 1, 53121 Bonn, Germany

   • A. Vikas Aggarwal,
   • Alissa Idelson,
   • Daniel Kalle,
   • Stefan-S. Jester &
   • Sigurd Höger

2. Department of Physics and Astronomy, University of Utah, Salt Lake City, Utah 84112, USA

   • Alexander Thiessen &
   • John M. Lupton

3. Institut für Experimentelle und Angewandte Physik, Universität Regensburg, Universitätsstrasse 31, D-93040 Regensburg, Germany

   • Dominik Würsch,
   • Thomas Stangl,
   • Florian Steiner,
   • Jan Vogelsang &
   • John M. Lupton

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SMILES: CCCCCCCCOC(C=C(C#C[Si](C(C)C)(C(C)C)CCCC#N)C(OCCCCCCCC)=C1)=C1C#CC2=CC3=C(C=C2)C4=C(C=C(C#CC5=C(OCCCCCCCC)C=C(C#C[Si](C(C)C)(C(C)C)CCCC#N)C(OCCCCCCCC)=C5)C=C4)N3C(C=C6)=CC=C6C(C=C7)=CC=C7C#CC(C=C8OCCCCCCCC)=C(OCCCCCCCC)C=C8C#CC(C=C9)=CC=C9C%10=C(C%11=CC=C(C#CC%12=C(OCCCCCCCC)C=C(C#CC%13=CC=C(C%14=CC=C(N%15C(C=C(C#CC%16=CC(OCCCCCCCC)=C(C#C[Si](C(C)C)(C(C)C)CCCC#N)C=C%16OCCCCCCCC)C=C%17)=C%17C%18=C%15C=C(C#CC%19=CC(OCCCCCCCC)=C(C#C[Si](C(C)C)(C(C)C)CCCC#N)C=C%19OCCCCCCCC)C=C%18)C=C%14)C=C%13)C(OCCCCCCCC)=C%12)C=C%11)C(C%20=CC=C(C#CC%21=C(OCCCCCCCC)C=C(C#CC%22=CC=C(C%23=CC=C(N%24C(C=C(C#CC%25=C(OCCCCCCCC)C=C(C#C[Si](C(C)C)(C(C)C)CCCC#N)C(OCCCCCCCC)=C%25)C=C%26)=C%26C%27=C%24C=C(C#CC%28=C(OCCCCCCCC)C=C(C#C[Si](C(C)C)(C(C)C)CCCC#N)C(OCCCCCCCC)=C%28)C=C%27)C=C%23)C=C%22)C(OCCCCCCCC)=C%21)C=C%20)=C(C%29=CC=C(C#CC%30=CC(OCCCCCCCC)=C(C#CC%31=CC=C(C%32=CC=C(N%33C(C=C(C#CC%34=C(OCCCCCCCC)C=C(C#C[Si](C(C)C)(C(C)C)CCCC#N)C(OCCCCCCCC)=C%34)C=C%35)=C%35C%36=C%33C=C(C#CC%37=C(OCCCCCCCC)C=C(C#C[Si](C(C)C)(C(C)C)CCCC#N)C(OCCCCCCCC)=C%37)C=C%36)C=C%32)C=C%31)C=C%30OCCCCCCCC)C=C%29)C(C%38=CC=C(C#CC%39=C(OCCCCCCCC)C=C(C#CC%40=CC=C(C%41=CC=C(N%42C(C=C(C#CC%43=CC(OCCCCCCCC)=C(C#C[Si](C(C)C)(C(C)C)CCCC#N)C=C%43OCCCCCCCC)C=C%44)=C%44C%45=C%42C=C(C#CC%46=CC(OCCCCCCCC)=C(C#C[Si](C(C)C)(C(C)C)CCCC#N)C=C%46OCCCCCCCC)C=C%45)C=C%41)C=C%40)C(OCCCCCCCC)=C%39)C=C%38)=C%10C%47=CC=C(C#CC%48=C(OCCCCCCCC)C=C(C#CC%49=CC=C(C%50=CC=C(N%51C(C=C(C#CC%52=C(OCCCCCCCC)C=C(C#C[Si](C(C)C)(C(C)C)CCCC#N)C(OCCCCCCCC)=C%52)C=C%53)=C%53C%54=C%51C=C(C#CC%55=CC(OCCCCCCCC)=C(C#C[Si](C(C)C)(C(C)C)CCCC#N)C=C%55OCCCCCCCC)C=C%54)C=C%50)C=C%49)C(OCCCCCCCC)=C%48)C=C%47

Scheme 1. Diene-Transmissive Diels–Alder Cycloaddition Sequences of [3]- and [4]Dendralene with the Prototypical Olefinic Dienophile

The first synthesis of all five possible monomethylated [4]dendralenes has been achieved via two distinct synthetic strategies. The Diels–Alder chemistry of these new dendralenes (as multidienes) with an electron poor dienophile, N-methylmaleimide (NMM), has been studied. Thus, simply upon mixing the dendralene and an excess of dienophile at ambient temperature in a common solvent, sequences of cycloadditions result in the rapid generation of complex multicyclic products. Distinct product distributions are obtained with differently substituted dendralenes, demonstrating that dendralene substitution influences the pathway followed, when a matrix of mechanistic possibilities exists. Dendralene site selectivities are traced to electronic, steric and conformational effects, thereby allowing predictive tools for applications of substituted dendralenes in future synthetic endeavors.

Scheme 2. Diene-Transmissive Diels–Alder Cycloaddition Sequences of [4]Dendralene (1) with the Dienophile N-Methylmaleimide (NMM)

Scheme 3. Syntheses of the Five Mono-Methyl-Substituted-[4]Dendralenes

3 Diels-Alder reactions in 1 go

 
FROM https://naturalproductman.wordpress.com/2016/01/29/11137/

Tris-adduct 36

An analytic sample of 36 was obtained by recrystallization from EtOAc/hexane to give colorless needles, mp 255–257 °C; R_f 0.20 (EtOAc, 100%);  

 

¹H NMR (300 MHz, CDCl₃) δ 3.22 (dd, J = 8.6, 5.9 Hz, 1H), 3.19–3.07 (m, 3H), 3.04–2.91 (m, 5H), 2.90 (s, 6H), 2.86 (s, 3H), 2.65 (ddd, J = 14.1, 13.4, 5.4 Hz, 1H), 2.35 (ddd, J = 14.3, 5.0, 2.5 Hz, 1H), 2.16–2.05 (m, 2H), 2.03–1.91 (m, 1H), 1.85–1.74 (m, 1H), 1.54 (d, J = 6.8 Hz, 3H) ppm;  

 

¹³C NMR (75 MHz, CDCl₃) δ 179.7 (C), 178.5 (C), 178.4 (C), 178.3 (C), 177.0 (C), 176.6 (C), 130.8 (C), 130.8 (C), 44.4 (CH), 43.4 (CH), 40.8 (CH), 40.6 (CH), 40.3 (CH), 39.2 (CH), 38.8 (CH), 33.7 (CH), 29.0 (CH), 25.0 (CH₃), 24.9 (CH₃), 24.8 (CH₃), 24.7 (CH₂), 24.4 (CH₂), 23.1 (CH₂), 16.5 (CH₃) ppm; 

 

 

IR (KBr disc) ν_max = 2961, 2948, 2842, 1770, 1695, 1435, 1383, 1286 cm^–1; 

 

 

LRMS (70 eV, EI) m/z (%) 453 ([M]^+•, 100%), 438 (7), 342 (33), 256 (14), 112 (39); 

 

 

HRMS calc for C₂₄H₂₇N₃O₆ [M]^+• 453.1900, found 453.1905.

Synthesis and Diels–Alder Reactivity of Substituted [4]Dendralenes

Mehmet F. Saglam^†, Ali R. Alborzi^†, Alan D. Payne^†, Anthony C. Willis^†, Michael N. Paddon-Row^‡, and Michael S. Sherburn^*†

^† Research School of Chemistry, The Australian National University, Canberra, ACT 2601, Australia

^‡ School of Chemistry, The University of New South Wales, Sydney, NSW 2052, Australia

J. Org. Chem., Article ASAP

DOI: 10.1021/acs.joc.5b02583

Publication Date (Web): January 12, 2016

Copyright © 2016 American Chemical Society

*E-mail: michael.sherburn@anu.edu.au.

 http://pubs.acs.org/doi/full/10.1021/acs.joc.5b02583

ACS Editors' Choice - This is an open access article published under an ACS AuthorChoice License, which permits copying and redistribution of the article or any adaptations for non-commercial purposes.

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Reductive amination of furfural to furfurylamine using aqueous ammonia solution and molecular hydrogen: an environmentally friendly approach

Green Chem., 2016, 18,487-496
DOI: 10.1039/C5GC01352F, Paper

Maya Chatterjee, Takayuki Ishizaka, Hajime Kawanami
An efficient process was developed to obtain furfurylamine with very high yield ([similar]92%) through the reductive amination of furfural under a mild reaction condition.

Reductive amination of furfural to furfurylamine using aqueous ammonia solution and molecular hydrogen: an environmentally friendly approach

 http://pubs.rsc.org/en/Content/ArticleLanding/2016/GC/C5GC01352F?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed%3A+rss%2FGC+%28RSC+-+Green+Chem.+latest+articles%29#!divAbstract

A simple and highly efficient method was developed for the transformation of furfural (a biomass derived aldehyde) to furfurylamine by reductive amination using an aqueous solution of ammonia and molecular hydrogen as an amine source and a reducing agent, respectively. By choosing a suitable catalyst, such as Rh/Al₂O₃, and reaction conditions, a very high selectivity of furfurylamine (∼92%) can be achieved within the reaction time of 2 h at 80 °C. A detailed analysis of the reaction system sheds some light on the reaction pathway and provides an understanding about each elementary step. The reaction was believed to proceed via an imine pathway although no such intermediate was detected because of the highly reactive nature. Optimization of different reaction parameters such as hydrogen pressure, temperature and substrate/ammonia mole ratio is shown to be critical to achieve high selectivity of furfurylamine. Time-dependent reaction profiles suggested that a Schiff base type intermediate was in the detectable range, which offers indirect evidence of the formation of imine. Competitive hydrogenation and amination of an aldehyde group were strongly dictated by the nature of the metal used. The studied protocol represents an environmentally benign process for amine synthesis, which can be effectively extended to the other aldehydes also. The studied catalyst could be recycled successfully without any significant loss of catalytic activity.

Reductive amination of furfural to furfurylamine using aqueous ammonia solution and molecular hydrogen: an environmentally friendly approach

Maya Chatterjee,*^a   Takayuki Ishizaka^a and  Hajime Kawanami*^ab  

*

Corresponding authors

^a

Microflow Chemistry Group, Research Institute for Chemical Process Technology, AIST Tohoku, 4-2-1, Nigatake, Miyagino-ku, Japan 
E-mail: c-maya@aist.go.jp, h-kawanami@aist.go.jp
Fax: +81 22 237 5388 
Tel: +81 22 237 5213

^b

CREST, Japan Science and Technology (JST), 4-1-8, Honcho, Kawaguchi, Japan

Green Chem., 2016,18, 487-496

DOI: 10.1039/C5GC01352F     /////////////

Hydrogenative cyclization of levulinic acid into [gamma]-valerolactone by photocatalytic intermolecular hydrogen transfer

.

Hydrogenative cyclization of levulinic acid into [gamma]-valerolactone by photocatalytic intermolecular hydrogen transfer

Green Chem., 2016, Advance Article
DOI: 10.1039/C5GC02971F, Communication

Hongxia Zhang, Min Zhao, Tianjian Zhao, Li Li, Zhenping Zhu
A hydrogenation-dehydrogenation coupling process efficiently realized an intermolecular hydrogen transfer from isopropanol to LA under photocatalytic conditions over gold-loaded TiO₂ catalysts.

 click
 http://pubs.rsc.org/en/Content/ArticleLanding/2016/GC/C5GC02971F?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed%3A+rss%2FGC+%28RSC+-+Green+Chem.+latest+articles%29#!divAbstract





 The hydrogenative cyclization of levulinic acid (LA) into γ-valerolactone (GVL) is an attractive route toward the use of renewable bio-sources but it normally suffers from the consumption of H₂. In this study, we report that an intermolecular hydrogen transfer from isopropanol to LA can be realized efficiently under photocatalytic conditions over gold-loaded TiO₂ catalysts. In this manner, isopropanol is dehydrogenated as acetone and pinacol with the total selectivity of >99%, whereas LA is hydrogenated and cyclized as GVL with the selectivity of up to 85%. In this reaction process, the production of GVL is mediated with hydrogenated dehydration of LA into an acetyl propionyl radical, which is further hydrogenated and cyclized as GVL. This hydrogenation–dehydrogenation coupling process provides an atom-economical green way for the conversion of LA into GVL.

Hydrogenative cyclization of levulinic acid into γ-valerolactone by photocatalytic intermolecular hydrogen transfer

Hongxia Zhang,*^ab   Min Zhao,^ab   Tianjian Zhao,^ab   Li Li^b and  Zhenping Zhu*^b  

*

Corresponding authors

^a

Institute of Application Chemistry, Shanxi University, Taiyuan 030006, China 
E-mail: hxzhang@sxu.edu.cn

^b

State Key Laboratory of Coal Conversion, Institute of Coal Chemistry, Chinese Academy of Sciences, Taiyuan 030001, China 
E-mail: zpzhu@sxicc.ac.cn

Green Chem., 2016, Advance Article

DOI: 10.1039/C5GC02971F

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Oxidative conversion of glucose to gluconic acid by iron(III) chloride in water under mild conditions

Green Chem., 2016, Advance Article
DOI: 10.1039/C5GC02614H, Communication

Hongdan Zhang, Ning Li, Xuejun Pan, Shubin Wu, Jun Xie
A simple method to oxidize glucose into gluconic acid in a concentrated FeCl₃ solution under mild conditions was developed

 click

http://pubs.rsc.org/en/Content/ArticleLanding/2016/GC/C5GC02614H?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed%3A+rss%2FGC+%28RSC+-+Green+Chem.+latest+articles%29#!divAbstract

.

Oxidative conversion of glucose to gluconic acid by iron(III) chloride in water under mild conditions

 

 

A simple method was demonstrated to oxidize glucose into gluconic acid in a concentrated FeCl₃ solution. 

The maximum gluconic acid yield (52.3%) was achieved in the 40% FeCl₃solution at 110 °C in 4 hours. 

Formic and acetic acids were the main coproducts with an yield of 10–20%.

Oxidative conversion of glucose to gluconic acid by iron(III) chloride in water under mild conditions

Hongdan Zhang,^abc   Ning Li,^b   Xuejun Pan,*^b   Shubin Wu*^c and   Jun Xie^a  

*

Corresponding authors

^a

Institute of New Energy and New Material, Key Laboratory of Energy Plants Resource and Utilization, Ministry of Agriculture, Key Laboratory of Biomass Energy of Guangdong Regular Higher Education Institutions, South China Agricultural University, Guangzhou 510642, P.R. China

^b

Department of Biological Systems Engineering, University of Wisconsin-Madison, 460 Henry Mall, Madison, USA
E-mail: xpan@wisc.edu
Tel: +1 (608) 262-4951

^c

State Key Laboratory of Pulp and Paper Engineering, South China University of Technology, Guangzhou 510640, P.R. China
E-mail: shubinwu@scut.edu.cn
Tel: +86 (020)22236808

Green Chem., 2016, Advance Article

DOI: 10.1039/C5GC02614H






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An efficient epoxidation of terminal aliphatic alkenes over heterogeneous catalysts: when solvent matters

An efficient epoxidation of terminal aliphatic alkenes over heterogeneous catalysts: when solvent matters

Catal. Sci. Technol., 2016, Advance Article
DOI: 10.1039/C5CY01639H, Paper

C. Palumbo, C. Tiozzo, N. Ravasio, R. Psaro, F. Carniato, C. Bisio, M. Guidotti
With a peculiar combination of catalyst/oxidant/solvent, it is possible to obtain good yields and excellent selectivities in the epoxidation of 1-octene.

see..............http://pubs.rsc.org/en/Content/ArticleLanding/2016/CY/C5CY01639H?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed%3A+rss%2Fcy+%28RSC+-+Catalysis+Science+%26+Technology+latest+articles%29#!divAbstract


The epoxidation of unfunctionalized terminal aliphatic alkenes over heterogeneous catalysts is still a challenging task. Due to the tuning of a peculiar catalyst/oxidant/solvent combination, it was possible to attain good alkene conversions (73%) and excellent selectivity values (>98%) in the desired terminal 1,2-epoxide. Over the titanium–silica catalyst and in the presence of tert-butylhydroperoxide, the use of α,α,α-trifluorotoluene as an uncommon non-toxic solvent was the key factor for a marked enhancement of selectivity. The titanium–silica catalyst was efficiently recycled and reused after a gentle rinsing with fresh solvent.

An efficient epoxidation of terminal aliphatic alkenes over heterogeneous catalysts: when solvent matters

C. Palumbo,^a   C. Tiozzo,^a   N. Ravasio,^a   R. Psaro,^a   F. Carniato,^b  C. Bisio^ab and   M. Guidotti*^a  

*

Corresponding authors

^a

CNR-Istituto di Scienze e Tecnologie Molecolari, Via C. Golgi 19, 20133 Milano, Italy
E-mail: m.guidotti@istm.cnr.it

^b

Dipartimento di Scienze e Innovazione Tecnologica and Nano-SISTEMI Interdisciplinary Centre, Università del Piemonte Orientale “A. Avogadro”, Viale Teresa Michel 11, 15121 Alessandria, Italy

Catal. Sci. Technol., 2016, Advance Article

DOI: 10.1039/C5CY01639H

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