요오드와 사이오설포네이트를 이용한 바이닐 설폰의 합성 = I2-mediated synthesis of vinyl sulfones using thiosulfonates

국문 초록 (Abstract)

Vinyl sulfone은 Chagas병의 치료제와 고분자 그리고 다양한 유기반응의 전구체로써 활용가치가 높다. 이러한 vinyl sulfone은 다양한 sulfone 화합물로부터 합성할 수 있다. 하지만 기존의 sulfone을 합성하기 위해서는 다루기 어려운 이산화황 가스나 DABSO와 같은 물질이 사용되었다. 본 연구가 진행되기 이전에 싸이올로부터 S-phenyl benzenethiosulfonate를 합성하는 연구가 진행되었다. 이 방법은 이산화황 기체를 직접 사용하지 않아 비교적 다루기 쉽고 친환경적이며 가격이 비싸지 않아 경제적이다. 본 연구에서는 이렇게 합성된 S-phenyl benzenethiosulfonate을 이용하여 요오드와 염기만을 사용하는 조건에서 vinyl sulfone을 합성하고자 하였다. S-phenyl benzenethiosulfonate 와 Styrene 또는 cinnamic acid의 교차 짝지음 반응을 통하여 다양한 작용기를 가지는 vinyl sulfone 화합물을 합성 하였다. 또한 메커니즘을 증명하기 위한 실험을 진행 하였고 그 결과를 토대로 가능한 메커니즘을 제시하였다.

목차 (Table of Contents)

• 1. Introduction ············································································1
• 2. Result and discussion ·······························································4
• 1) Synthesis of vinyl sulfone using styrene ························4
• (1) Optimization ·······························································4
• (2) Substrate scope ·······························································9
• 2) Synthesis of vinyl sulfone using cinnamic acid ········13
• (1) Optimization ·····························································13
• (2) Substrate scope ·····························································15
• 3) Mechanism study ·····························································17
• (1) Styrene ··········································································17
• (2) Cinnamic acid ·····························································19
• (3) Plausible mechanism ················································20
• 3. Conclusion ·······················································································22
• 4. Reference ·······················································································23
• 5. Experimental section ·····························································25
• 1) Synthesis of vinyl sulfone ················································25
• 2) Analysis data ··········································································26