Iodohydroxylation of alkylidenecyclopropanes. An efficient synthesis of iodocyclopropylmethanol and 3-iodobut-3-en-1-ol derivatives.

doi:10.1021/jo800123m

Paper

Iodohydroxylation of alkylidenecyclopropanes. An efficient synthesis of iodocyclopropylmethanol and 3-iodobut-3-en-1-ol derivatives.

Published May 24, 2008 · Yewei Yang, Xian Huang*

The Journal of organic chemistry

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21

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1

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Abstract

A variety of iodocyclopropylmethanol and 3-iodobut-3-en-1-ol derivatives were readily prepared in good to excellent yields via the simple iodohydroxylation reaction of alkylidenecyclopropanes with I(2) and H(2)O. An unexpected rearrangement to give 4-hydroxy-1,2-diphenyl-butan-1-one derivatives was observed compared to the halohydroxylation products.

Study Snapshot

This study demonstrates an efficient synthesis of iodocyclopropylmethanol and 3-iodobut-3-en-1-ol derivatives from alkylidenecyclopropanes, with unexpected rearrangements to 4-hydroxy-1,2-diphenyl-butan-1-one derivative

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Iodohydroxylation of alkylidenecyclopropanes. An efficient synthesis of iodocyclopropylmethanol and 3-iodobut-3-en-1-ol derivatives.

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References

Citations

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Substituent effects significantly influence the equilibrium between cyclopropylcarbinyl, bicyclobutonium, cyclobutyl, and homoallyl cations, with electron-donating groups favoring specific structures and electron-withdrawing groups causing shallower potential energy surfaces.

Transformation of Unactivated Alkenes into Iodohydrins and β‐Iodoethers using Iodine‐DMSO as a Reagent Combination

Iodine and DMSO effectively transform unactivated alkenes into iodohydrins and iodoethers with up to 86% yield in MeCN solvent.

A ligand-controlled switch of regioselectivity in ring-opening coupling of diarylmethylenecyclopropa[b]naphthalenes with Grignard reagents.

Pd(OAc)2 ligand effectively switches regioselectivity in ring-opening coupling of diarylmethylenecyclopropa[b]naphthalenes with Grignard reagents, providing differently substituted -vinylic naphthalene

Studies on the regio- and diastereo-selective epoxidation of daphnanes and tiglianes.

This study presents an efficient, potentially general, -epoxidation method for daphnanes and tiglianes, enabling the study of their biological activities and potential applications in protein kinase C signaling.

Hot water-promoted cyclopropylcarbinyl rearrangement facilitates construction of homoallylic alcohols.

Hot water-promoted cyclopropylcarbinyl rearrangement provides high chemical yields for synthesizing homoallylic alcohols, particularly ring-expanded cyclic homoallylic alcohols, in a refluxing 9:1 (v/v) H2O-1