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Conversion of pinane skeleton into strained bicyclo[2.1.1] hexane system. Pinacol-type rearrangement of α-pineneglycol tosylate

✍ Scribed by Takayuki Suga; Toshifumi Hirata; Tsuyoshi Shishibori; Tamon Matsuura

Publisher: Elsevier Science
Year: 1968
Tongue: French
Weight: 135 KB
Volume: 9
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)75559-6

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✦ Synopsis

OGPIneneglyaol monotoeylete II derived from I (1) wee treated with methenollc poteaslum hydroxide.

The main product from II was found 1968) to be a member of the blcyclo[2.1.4 hexane series. This observation Is the first example of ring contraction of a member of the plnane group to this highly strained ring system. ols-&Pineneglyool monotoeylete (II), m.p. 75-76'~, wee treated with methenolic potassium hydroxide in methanol at 65'C for 3 hrs. An oily reaction mixture was obtained, which wee subjected to gee chromatography (colunm: DEGS, NGS, end PEG-6000), thin-layer chromatography, and then elution ohromatography on a eilicagel CO~UIVIII. In thla manner, the reaction mixture wae found

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Pinacol-type rearrangements in the pinan

Pinacol-type rearrangements in the pinane series: a facile entry into the bicyclo[2.1.1]hexane system

✍ Robert G. Carlson; James K. Pierce 📂 Article 📅 1968 🏛 Elsevier Science 🌐 French ⚖ 160 KB

In spite of the current interest in the highly strained bicyclo[2.l.llhexane system, there is no efficient, non-photochemical synthesis of this system from readily available compounds.