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Dergiler / Turkish Journal of Chemistry / 2004 / Cilt: 28 - Sayı: 2

Cationic Rearrangements of an endo}-Cyclopropyl Methanol System Incorporated in a Benzonorbornadiene System

Abdullah MENZEK
Melek KARAKAYA
Sayfa
141–148
Yayın Tarihi
2004-02-01
DOI
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⚡ TL;DR(1 Cümlede Hızlı Çıkarım)

The behaviour of 20 differs from that of exo isomer 14, probably due to the nature of the intermediates in these reactions.

📌 3 Maddede Bu Makale

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Amaç & Hipotez:Chloride 18 (47%) and alcohol 21 (44%) were isolated from the reaction of alcohol 20 with SOCl2.
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Temel Bulgular & Veri:Cyclopropylcarbinyl -- cyclopropylcarbinyl rearrangement leads to chloride 22, which hydrolyses on separation to give alcohol 21.
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Sonuç & Katkı:The behaviour of 20 differs from that of exo isomer 14, probably due to the nature of the intermediates in these reactions.
🔬Tür:Araştırma Makalesi
📍Kapsam:Genişletilmiş Akademik Örneklem
⚙️Değişkenler:Alcohols · Benzohomonorbornadiene · Halogenation

Özet

Chloride 18 (47%) and alcohol 21 (44%) were isolated from the reaction of alcohol 20 with SOCl2. Cyclopropylcarbinyl -- cyclopropylcarbinyl rearrangement leads to chloride 22, which hydrolyses on separation to give alcohol 21. Chloride 18 results from cyclopropyl -- allylcarbinyl rearrangement, followed by a 1,2 -- aryl shift (sequential rearrangement). Syntheses of compounds 23 and 24 support the structures. The behaviour of 20 differs from that of exo isomer 14, probably due to the nature of the intermediates in these reactions.

Abstract

Chloride 18 (47%) and alcohol 21 (44%) were isolated from the reaction of alcohol 20 with SOCl2. Cyclopropylcarbinyl -- cyclopropylcarbinyl rearrangement leads to chloride 22, which hydrolyses on separation to give alcohol 21. Chloride 18 results from cyclopropyl -- allylcarbinyl rearrangement, followed by a 1,2 -- aryl shift (sequential rearrangement). Syntheses of compounds 23 and 24 support the structures. The behaviour of 20 differs from that of exo isomer 14, probably due to the nature of the intermediates in these reactions.

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Bu Makaleye Atıf Yap

MENZEK, A., KARAKAYA, M. (2004). Cationic Rearrangements of an endo}-Cyclopropyl Methanol System Incorporated in a Benzonorbornadiene System. Turkish Journal of Chemistry, Cilt: 28 - Sayı: 2, 141–148. https://ajindex.com/articles/185485

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