Woodward cis-hydroxylation
In today's world, Woodward cis-hydroxylation is a topic that has captured the attention and interest of millions of people around the world. Whether due to its impact on society, its relevance in popular culture or its importance in history, Woodward cis-hydroxylation has managed to transcend borders and generations, becoming a topic of discussion and debate in different areas. From its emergence to the present, Woodward cis-hydroxylation has left its mark on people's lives, marking a before and after in the way we see the world. In this article, we will explore the different aspects and dimensions of Woodward cis-hydroxylation, analyzing its influence in various fields and its role in contemporary society.
| Woodward cis-hydroxylation | |
|---|---|
| Named after | Robert Burns Woodward |
| Reaction type | addition reaction |
| Identifiers | |
| Organic Chemistry Portal | woodward-reaction |
The Woodward cis-hydroxylation (also known as the Woodward reaction) is the chemical reaction of alkenes with iodine and silver acetate in wet acetic acid to form cis-diols.(conversion of olefin into cis-diol)
The reaction is named after its discoverer, Robert Burns Woodward.
This reaction has found application in steroid synthesis.
Reaction mechanism
The reaction of the iodine with the alkene is promoted by the silver acetate, thus forming an iodinium ion (3). The iodinium ion is opened via SN2 reaction by acetic acid (or silver acetate) to give the first intermediate, the iodo-acetate (4). Through anchimeric assistance, the iodine is displaced via another SN2 reaction to give an oxonium ion (5), which is subsequently hydrolyzed to the give the mono-ester (6).
References
- ^ Woodward, R. B., U.S. patent 2,687,435
- ^ Woodward, R. B.; Brutcher, F. V. (1958). "cis-Hydroxylation of a Synthetic Steroid Intermediate with Iodine, Silver Acetate and Wet Acetic Acid". J. Am. Chem. Soc. 80 (1): 209–211. doi:10.1021/ja01534a053. ISSN 0002-7863.
- ^ Mangoni, L.; Dovinola, V. (1969). "The stereochemistry of woodward cis-hydroxylation in some steroidal olefins". Tetrahedron Letters. 10 (60): 5235–5238. doi:10.1016/S0040-4039(01)88931-0. ISSN 0040-4039.