Robinson Annulation Mechanismbetween 2 Methylcyclohexene And Methyl Vinyl Ketone

1 michael addition 2 intramolecular aldol condensation.

Robinson annulation mechanismbetween 2 methylcyclohexene and methyl vinyl ketone. These are organic compounds containing a ketone that is conjugated to a cyclic moiety. Michael addition of cyclohexanones to methyl vinyl ketone followed by intramolecular aldol condensation to afford six membered α β unsaturated ketones. Pubmed the action of t butyl hypochlorite on 1 methyl 4 isopropyl 3 cyclohexene p menthene 3. The cyclodehydration of 3 catalyzed by l proline is then performed at 25 c by simple stirring under argon for 120 h.

2 methylcyclohexanone exists as a liquid slightly soluble in water and an extremely weak basic essentially neutral compound based on its pka. Robinson annulation is a fundamental organic reaction in particular because it is at the base of the synthesis of steroids and other important molecules even of pharmaceutical interest. The newly formed enolate intermediate must first tautomerize for the conversion to continue. As illustrated in the following figure the robinson annulation reaction involves two steps the first step involves the michael addition of a ketone enolate the enolate derived from cyclohexanone in the example pictured below to an alpha beta unsaturated ketone methyl vinyl ketone below.

Mechanism of the robinson annulation. 2 methylcyclohexanone is a cyclic ketone that is reported to occur in mint and horse chestnut. 3 methyl 2 cyclohexen 1 one also known as mch or fema 3360 belongs to the class of organic compounds known as cyclohexenones. The first step in the process is the michael addition to an α β unsaturated ketone such as methyl vinyl ketone ethyl vinyl ketone is shown above.

2 methylcyclohexanone also known as fema 3946 or tetrahydro o cresol belongs to the class of organic compounds known as cyclic ketones. Investigation in the field of stereochemistry of polycyclic compounds monoesters of cis and trans 1 methyl 1 2 cyclohexanedicarboxylic acids or 1 methyl 4 cyclohexene 1 2 dicarboxylic acids and their conversion. The reaction involves two important steps. Cyclohexenones are compounds containing a cylohexenone moiety which is a six membered aliphatic ring that carries a ketone and has one endocyclic double bond.

In a second step the methyl group adjacent to the carbonyl is deprotonated and undergoes an. The annulation reaction has as its most common substrates generally cycle hexanone and methyl vinyl ketone. The optimized procedure 6 2 methyl 2 3 oxobutyl 1 3 cyclohexanedione 3 is prepared by heating 2 methylcyclohexane 1 3 dione 2 with methyl vinyl ketone 1 in aqueous acetic acid at 75 c for 1 h after which 3 is purified.