1,1-Diphenyl-2-vinylcyclopropane was synthesized and its spectral properties and photochemical reactions were studied to test the ability of the cyclopropane ring to extend or transmit conjugation.
The spectral properties indicate that the cyclopropane ring is in conjugation with the vinyl and/or the phenyl ring to some extent but it does not transmit the conjugation.
When the compound is irradiated with 253.7 nm light in quartz tube, 1,1-diphenylethylene is formed as a major product and a small amount of 4,4-diphenylcyclopentene. Sensitized photoreactions show quite different phenomena from that of conjugated dienes and trienes supporting the spectral results that the cyclopropane ring does not transmit the conjugation.
1,1-디페닐-2-비닐시클로프로판의 광화학 반응 생성물을 확인한 결과는 1,1-디페닐에티렌 및 4,4-디페닐시클로펜텐이며 그외에 적은 양의 미지의 물질들이 있다. 이 화합물 I의 시클로프로판 고리는 비닐기 및 벤젠 고리와 걸러 짝짓기가 이루어지나 시클로프로판 고리를 통한 걸러 짝짓기는 이루어지지 않는다. 증감제로 벤조페논을 썼으며 광이성질화 반응이 주로 일어나며, 주생성물 1,1-디페닐에티렌은 쪼개져 생기고 4,4-디페닐 시클로펜텐은 자리 옮김 반응으로 생성된다.
