Nadic anhydride

endo

exo

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Names
Systematic IUPAC name

24-oxatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione

Other names

5-Norbornene-2,3-dicarboxylic anhydride
Nadic acid anhydride
Himic anhydride (exo)
Carbic anhydride (endo)

Identifiers

CAS Number

* 826-62-0 Y
* 2746-19-2 (exo) Y
* 129-64-6 (endo) Y

3D model (JSmol)

* Interactive image

ChemSpider |

* 12668 Y

EC Number |

* 212-557-9

PubChem CID

* 13223

InChI

* InChI=1S/C9H8O3/c10-8-6-4-1-2-5(3-4)7(6)9(11)12-8/h1-2,4-7H,3H2 Y

Key: KNDQHSIWLOJIGP-UHFFFAOYSA-N Y

* InChI=1S/C9H8O3/c10-8-6-4-1-2-5(3-4)7(6)9(11)12-8/h1-2,4-7H,3H2

Key: KNDQHSIWLOJIGP-UHFFFAOYSA-N

SMILES

* C1C2C=CC1C3C2C(=O)OC3=O

Properties

Chemical formula

| C9H8O3
Molar mass | 164.160 g·mol−1
Appearance  | white solid

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

Tracking categories (test):

* SizeSet
* PairSizeSet

Nadic anhydride, also known as 5-norbornene-2,3-dicarboxylic anhydride, is an organic acid anhydride derivative of norbornene.

## Contents

* 1 Stereochemistry
* 2 Preparation
* 3 Uses
* 4 References

## Stereochemistry

Nadic anhydride exhibits endo-exo isomerism. In the exo isomer, the acid anhydride group points in the same direction towards the bridging carbon of the norbornene, while in the endo isomer the acid anhydride group points in the opposite direction. These isomers are respectively named cis-5-norbornene-exo-2,3-dicarboxylic anhydride (also known as himic anhydride) and cis-5-norbornene-endo-2,3-dicarboxylic anhydride (also known as carbic anhydride).[1][2] Commercially available nadic anhydride is mainly the endo isomer, as this is the isomer predominantly made in the Diels-Alder reaction in its synthesis.[3]

160px | 160px

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160px | 160px
endo | exo

## Preparation

In the patent for the Diels-Alder reaction, nadic anhydride was given as an example of the reaction, made by the addition of maleic anhydride to cyclopentadiene, which gives mostly the endo isomer.[3] The endo isomer can be converted into the exo isomer by irradiation with UV light.[4]

## Uses

Due to the reactivity of the norbornene moiety in the thiol-ene reaction, nadic anhydride is used in the synthesis of monomers for cross-linked polymer networks based on thiol-ene linkages.[5]

## References

1. ↑ Template:Cite PubChem
2. ↑ Template:Cite PubChem
3. ↑ 3.0 3.1 & Kurt Alder"Organic compound having hydrogenated ring systems and process of preparing it" StatesUS1944731A United States patent US1944731A, published January 23, 1934
4. ↑ Pandey, Bipin; Athawale, Asawar A.; Reddy, Ravinder S.; Dalvi, Pravinder S.; Kumar, Pradeep (1991). "A Remarkably Efficient Photochemical Methodology for Endo to Exo IsomerizatLon of Dials–Alder Cycloadducts". Chemistry Letters 20 (7): 1173–1176. doi:10.1246/cl.1991.1173.
5. ↑ Hoyle, Charles E.; Bowman, Christopher N. (2010). "Thiol–Ene Click Chemistry". Angewandte Chemie International Edition 49 (9): 1540–1573. doi:10.1002/anie.200903924.

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*[CID]: Compound ID