# Unusual Rearrangements in Cyclohex-3-ene-1-carboxamide Derivatives: Pathway to Bicyclic Lactones

## TL;DR

This paper describes a new method to synthesize bicyclic lactone derivatives through rearrangements in cyclohex-3-ene-1-carboxamide compounds.

## Contribution

A new and applicable method for synthesizing bicyclic lactone derivatives via bromination and epoxidation reactions is developed.

## Key findings

- Bromination and epoxidation reactions produced substituted bicyclic lactone compounds as rearrangement products.
- Hydroxymethyl and amide groups on the cyclohexene ring significantly influenced product formation.
- Spectroscopic methods confirmed the structures of the synthesized compounds.

## Abstract

The synthesis of new bicyclic lactone derivatives was
carried out
starting from 2-methyl/phenyl-3a,4,7,7a-tetrahydro-1H-isoindole-1,3(2H)-dione. 6-(Hydroxymethyl)-N-methyl/phenylcyclohex-3-ene-1-carboxamide
derivatives were obtained from the reduction of tetrahydro-1H-isoindole-1,3(2H)-diones with NaBH4. Bromination and epoxidation reactions of both compounds
were examined, and the structures of the resulting products were determined
by spectroscopic methods. Substituted bicyclic lactone compounds,
which are interesting rearrangement products in both bromination and
epoxidation reactions, were obtained. In particular, hydroxymethyl
(−CH2OH) and amide (−CONHR) groups attached
to the cyclohexene ring in the bromination and epoxidation reactions
were found to be effective in product formation. As a result, a new
and applicable method was developed for the synthesis of bicyclic
lactone derivatives.