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Trends in Diels Alder in Polymer Chemistry

Benoi

Institut Charles Gerhardt, CNRS,

Diels opinion 2

Content

1. Preamble

2. Generalities

2.1 Introduction

2.2 Cycloaddition

2.3 Electronic effects of the Diene/Dienophile in Diels

2.4 Furan/Maleimide (F/M) couple.

2.4.1 Generalities about furan and maleimide

2.4.2 Polyaddition of furan

2.4.3 Networks

2.4.4 Miscellaneous an

2.4.5 DA for self

2.4.6 Shape

2.4.7 H

2.4.8

2.4.9. Sealant cured on demand

2.4.10 DA in health

3. Other diene/die

3.1. Petro

3.1.1 Cyclodienes and cyclopentadienes

3.1.2 Acyclic dienes

3.1.3 Anthracene

3.2 Bio

3.2.1 Sorbic acid and derivatives

3.2.

3.2.3 Myrcene and Farnesene

3.2.4 Eugenol and Cardanol

3.3 Dienophiles.

3.3.1 Maleic anhydri

3.3.2. Acrylic acid and derivatives

3.3.3 Vinyl ketones

3.3.4. Itaconic acid, citraconic acid and their derivatives

4. Discussion and outlooks

3

References

1. Preamble

Durmaz, Colakoglu, Tunca and Hizal [1]

rather than conventional paints, [, and adhesives. [has been the pioneer in that area and has comprehensive 4

Due to our specific self

[, repairing coatings[ decided to upda 2 2 [. The application of the DA reaction into polymer synthesis

Figure )

5

Figure

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Number of publicaton

Years 6 2

ʌorbital

Figure ).

7

Figure

[. The [. However, the Gandini update 2 [, the electronic effect "normal electro [ Scheme 8

Scheme

Another case exists

[ Scheme ). This reaction is called

Scheme

This reverse reaction has change

Figure )

Figure )

9

Figure

10

Figure

The lFigure 4

11 [ Figure )[ [ )[(Figure )[ Figure ) [ Figure )[(Figure )

Figure

As for[ Figure )

[ Figure )

Figure

12 2 2 [8]. [pioneered its synthesis th

Scheme )

. Later, [. [.[ Scheme )

Scheme

Scheme ). Both types of

13

Scheme

The m

Scheme )

2 [(Figure ) [

Scheme

Scheme

14

Figure

[ Scheme 7) 15 antrodia camphorata [

Paecilomyces farinosus [ Scheme )

Scheme

to[. endodominates (as the kinetic product that is faster formed) exo, is thermodynamically favourited at higher temperature. The formation and endo exo [ 16 DA. [, the F/M couple take

Scheme ).

Scheme

It took 25 years before DA

Scheme ).

17

Scheme

[. This

Scheme ).

[, non [ [can be 18

Scheme

Another technique consists in developing po

Scheme ).

Scheme

Furthermore, i

Scheme ) [.

Scheme

19

Scheme )

Scheme

The F/M pair can also be used in the polymer field as a crosslinking agent

Figure

illustrates fives cycles and the sample was noted to be irreversible below 120 °C while at 130

Figure

20 [ [ Scheme ). [ Scheme )

Scheme

21
[with H2SO4 [ (Scheme ) or a thiol[(

Scheme ).

Scheme

magination [(Figure ).

Figure

[show 22

Scheme

[M[were DA adducts

Scheme )

23

Scheme

[ Scheme ).

Scheme

24

Scheme maleimide core containing 32

DA adduct of cyclopentadiene and acetylene, which is also a dienophile, as chain [. Then, a functionalities as chain 5H11 group. [ [and [, as

Figure

25

Figure

[h 26
[developed a polyurethane

Scheme )

Scheme

Figure )[ Figure )[.

27

Figure

°C water bath; (c, d, e) visual

28

Figure

In addition to this example, more and more

[, polycaprolactone[or epoxy resin [ [introduced the

Figure ). Indeed,

29

Figure

Sealant cured on demand

30
monocomponents [. Increasing the temperature via

Figure )[Aromatic

Figure

All 31
[, fluorescent sensor[ [it is easy to quickly [and more generally in chemical biology [

3. Other diene/dienophile couples

3.1. Petro

th 32
[. CPD dimerizes [. This (Indeed, pure CPD in situ

Scheme

Since the beginning of the 20th

[, such as quinones [, [, acrylate derivatives [, vinyl ketones [ [. DA reaction with ab initio [. Other studies [. Very recently, reactions of CPD with hexadienone [ [ Scheme ), enhancing the

Scheme cage

33
Figure ). Thiophene can be used as a diene or dienophile, but it is not very reactive [. In order to overcome this lack of reactivity, it is possible to substitute it [ [ Figure ). [. It

Figure

Less studies have been [

34

Scheme

ultra , as an

Figure

Figure

35
The same authors also proposed the inverse electron demand DielsAlder (IVED .Figure from Figure Alder reaction between tetrazines and strained alkenes igroupFigure ) and a lot of acyclic dienes can perform DA reactions [.

Figure

In addition, many articles have reported the use of acyclic dienes in hetero[ [, [ Scheme ) 36

Scheme

[ [(Figure ) or aza[(Figure

Figure r

Scheme ) which was first isolated in 1832 by Dumas and Laurent [.

Scheme

37

Scheme

[. This compound and [, carbonyls [ [ [, polyethylene , or new DA adduct [ N- [ N- 38

Scheme )

N,NǦௗyiel

ௗ 1.

DA) while the second one,

Scheme Alder polymers from the addition of dienes containing anthracene groups and [deals with

Scheme )

4 -. 39

Scheme

Interestingly, these authors also reported a model study from anthracene methyl

1H NMR spectro

Scheme )

40

Scheme

[, or in the synthesis of foldamer [ Scheme ). Another smart use of anthracene [ Scheme [graft [ [Although making use of readily 120 h
41

Scheme

Scheme b-b-

42

Figure

Schubert et al.

60.

Scheme ) The copolymer bearing methacrylate

43

Scheme

3.2 Bio

Figure ).

44

Figure

2 [, or other triazolines [, acrylonitrile [, aryne [, acrylate [ 45

Scheme

Figure ) and is

Figure

Muconic acid can

[or [. By intramolecular cyclization of muconic acid, it is possible to obtain [ -[ Figure ).

Figure

This acid is also well

[. It can be used as a monome 46

Scheme

Thanks to its two conjugated double bonds, muconic acid has been used for the [ Scheme ).

Scheme

Scheme )

Scheme

47
[. However, myrcene is mostly industrially produced from turpentine, the [. Myrcene is an acyclic monoterpene (Figure ) [. Since the first reaction between myrcene and maleic [, numerous DA reactions of myrcene have been reported with acrolein [, quinone[, acrylic acid and other various dienophiles . In 2013, the

Scheme ).

Scheme

As myrcene

alpina galanga . In Nature, farnesene is used by [. Other patents [, plasticizers for PVC [ [. Recently, farnesene has also been used 48

Scheme

Figure )

Fur [, epoxy resins [ . Eu [. The reaction of a dienophile on 49

Scheme ).

Scheme

[ [ Scheme ).

Scheme

50

Anacardium

[. Cardanol is

8%), monoene (4849%), diene (l617%) and triene (2930%) as

Cardanol and its derivatives can be found in many area of materials [ [, surfactants [ [) or [, epoxy curing agents[, coatings [, composites [ [. Thanks to the same mechanism [, and the synthesis of coating binders [, epoxy resins [, or reactive amides [ [

Scheme

). In this particular case, cardanol acts as both a diene and a dieno

Scheme

3.3.2.

3.3 3.3 51

Scheme ), were first prepared in 1830 [

Scheme

Many examples of DA reactions involving maleic anhydride and its derivatives as dienophi [, furan [, some vegetable oils [, [, and numerous other dienes [. Nowadays, [. (Scheme ).

Fumaria officinalis,

Scheme 1 2

52
[. Acrylic Figure ) are [, poly(methacrylate)s [.

Figure

The [ [. Another example deals with the [. More

Figure ) from a DA reaction between

[a [ [, showing the renewed interest of acrylic acid and its derivatives in the 53

Figure

Moreover, these monomers could be synthesized from renewable raw materials as lactic acid [, glycerol via [via dehydration into acrolein [, [, strengthening its position in the industry

Scheme .

Scheme

Figure ) are ketones bearing double bonds which enable DA [, ii) thermal elimination of 54
- [, iii) addition of vinyl [ [. However, the most common strategy is the cross [ [, that is

Figure

Scheme ) [,

[ [. Recently,

Scheme

55
Aspergillus itaconicus [. Itaconic acid and its

Figure ) have been lately used for DA purposes.

Figure

Some [, or with oxazolones [, itaconic [, or, more recently, with isopropene[or furan [

Scheme ).

Scheme

Citraconic acid could also be synthesized from citric [. DA reactions . However, most 56
Figure 3) are devoted to citraconimide molecules. In the 90s, the crosslinking reaction of [. The synthesis of azasteroides was [. Wang[

Scheme )

Scheme

Of course, this enumeration of other dienophiles involved in DA reaction is not exhaustive. [, cycloalkenones [ [ [or as diene [.

4. Discussion and outlooks

insertion). The emergence and success of increasingly specialized 57
[. As described in the section 58
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