Селективные методы пероксидирования β-дикарбонильных соединений и их гетероаналогов тема диссертации и автореферата по ВАК РФ 02.00.03, кандидат химических наук Борисов, Дмитрий Александрович

• Борисов, Дмитрий Александрович
• кандидат химических наук
• 2011

Оглавление диссертации кандидат химических наук Борисов, Дмитрий Александрович

Введение.

Глава I. Синтез пяти- и шестичленных циклических пероксидов (литературный обзор).

1.1. Введение.

1.2. Синтез 1,2-диоксоланов.

1.3. Синтез 1,2,4-триоксоланов.

1.4. Синтез 1,2-диоксанов.

1.5. Синтез 1,2-диоксенов.

1.6. Синтез 1,2,4-триоксанов.

1.7. Синтез 1,2,4,5-тетраоксанов.

Введение диссертации (часть автореферата) на тему «Селективные методы пероксидирования β-дикарбонильных соединений и их гетероаналогов»

11.2. Селективный метод синтеза мостиковых 1,2,4,5-тетраоксанов.

Сильные кислоты как сорастворители и катализаторы присоединения пероксида водорода к р-дикетонам.105

11.3. Окисление замещенных Р-дикетонов пероксидом водорода. Синтез сложных эфиров через образование мостиковых 1,2,4,5-тетраоксанов.114

11.4. Катализированное переходными металлами (Cu, Fe, Мп, Со) пероксидирование p-дикарбонильных соединений третя-бутилгидропероксидом.118

11.5. Катализированное переходными металлами (Cu, Fe, Мп, Со) пероксидирование производных малонодинитрила и циануксусного эфира mjjew-бутилгидропероксидом.129

11.6. Заключение.137

Заключение диссертации по теме «Органическая химия», Борисов, Дмитрий Александрович

ВЫВОДЫ

1. В химии органических пероксидов предложены пути решения проблемы селективного пероксидирования р-дикарбонильных соединений и их гетероаналогов. Осуществлен синтез ранее недоступных структурных типов пероксидов.

2. Разработан удобный и простой в экспериментальном исполнении метод синтеза мостиковых 1,2,4,5-тетраоксанов, который позволяет получать эти соединения в граммовых количествах с выходом 44-79 %. Метод основан на кислотно-катализированной реакции р-дикетонов с пероксидом водорода. Ключевым фактором, определяющим выход и селективность образования 1,2,4,5-тетраоксанов является высокая концентрация сильной кислоты: H2SO4, HBF4 и НС104. Показана возможность модификации боковой цепи полученных соединений с сохранением 1,2,4,5-тетраоксанового цикла.

3. Обнаружено кислотно-катализированное окислительное превращение алкил- и бензилзамещенных Р-дикетонов в сложные эфиры под действием пероксида водорода, протекающее через стадию образования мостиковых 1,2,4,5-тетраоксанов.

4. Установлено, что переходные металлы (Си, Fe, Мп, Со) катализируют пероксидирование а-замещеных p-дикарбонильных соединений трет-бутилгидропероксидом в а-положение. На основе этой реакции реализован селективный и удобный в экспериментальном исполнении метод получения ранее недоступных а-шрет-бутилперокси-Р-дикарбонильных соединений. Синтезы легко масштабируются без снижения выхода целевых пероксидов, которые могут быть получены в граммовых количествах. Реакция применима к различным по структуре а-замещенным-р-дикарбонильным соединениям. С наибольшим выходом целевые пероксиды получаются из Р-кетоэфиров (до 90%), с несколько меньшим из р-дикетонов (до 72%) и малонатов (до 69%).

5. Впервые осуществлено селективное окисление а-замещенных производных малонодинитрила и циануксусного эфира в а-положение с образованием несимметричных а-тре/и-бутилпероксипроизводных. Обнаружено, что переходные металлы (Си, Fe, Мп, Со) катализируют пероксидирование а-замещеных производных малонодинитрила и циануксусного эфира итре/и-бутилгидропероксидом в а-положение. Метод пригоден для синтеза целевых пероксидов в граммовых количествах, с его помощью можно осуществлять пероксидирование различных по структуре а-замещенных производных малонодинитрила и циануксусного эфира. С наибольшим выходом целевые пероксиды образуются из производных малонодинитрила (до 94%), с меньшим — из производных циануксусного эфира (до 83%).

6. Получены вещества с высокой активностью по отношению к возбудителям распространённых гельминтных заболеваний — шистосомам (Schistosoma mansoni), фасциолам (Fasciola hepatica) и эхиностомам (Echinostoma caproni).

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