Question

The Diels-Alder reaction between butadiene and dim

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Concepts and reason

Diels – alder reaction is a [4 + 2] cycloaddition reaction between conjugated diene and dienophile (substituted alkene or alkyne) to form substituted cyclohexene. This reaction occurs in a single step with no intermediates.

Fundamentals

A compound with a conjugated double bond in a system is represented as diene.

Diene

A substituted alkene or alkyne is represented as dienophile.

н
н
нан
Dienophiles

Example:

According to stereochemistry,

Cis reactants lead to Cis products and Trans reactants leads to Trans products.

Consider the transition state of the reaction as shown below:

осна
OCH3
Transition state

The product of the reaction forms as follows:

OCH3
COCH3
CH3
(1R,28)-dimethyl cyclohex-4-ene-1,2-dicarboxylate
Transition state
OCH3
OCH3
dimethyl (1R,25)-cyclohex-4-ene-1

I
OCH
OCH
CI OCH
CH
II
I
OCH3
OCH
..., 1
OCH

Ans:

OCH3
OCH3
564
160°C
24h
OCH3
OCH3
(18,25)-dimethyl cyclohex-4-ene-1,2-dicarboxylate
+
Os
OCH3
OCH3
dimethyl (1R,25)-cyclohex-

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The Diels-Alder reaction between butadiene and dimethyl maleate yields a ring structure, as shown in the...
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