Siloxy-cope rearrangements of the trans-l-vinylcyclotridec-3-en-l-ol system

Graduate Thesis Or Dissertation

Public Deposited

Citeable URL: https://ir.library.oregonstate.edu/concern/graduate_thesis_or_dissertations/z890rz02k

Descriptions

Attribute Name	Values
Creator	Bolesta, Richard Edward
Abstract	The thermolysis of trans-1 -trimethylsiloxy- 1-vinylcyclotridec- 3-ene (VI-OTMS) led to the formation of two major products: 4-vinylcyclotridecanone (VII) and cyclopentadec-5-en-l-one (VIII) after hydrolysis. Ketone VII is produced by a concerted [3, 3] sigmatropic shift, while ketone VIII is formed by a [1, 3] sigmatropic shift with a concerted or diradical mechanism. The rates of reaction and activation parameters have been determined. The large amount of [3, 3] shift product formed hinders the use of the siloxy-Cope rearrangement as a two-carbon ring expansion reaction for the thirteen member ring systems. The synthetic scheme for the formation of 1-vinylcyclotridec- 3-ene-l-ol produces only the trans-isomer.
Resource Type	Masters Thesis
Date Available	2013-11-22T23:18:48+00:00
Date Issued	1975-08-11
Degree Level	Master's
Degree Name	Master of Science (M.S.)
Degree Field	Chemistry
Degree Grantor	Oregon State University
Commencement Year	1976
Advisor	Thies, Richard W.
Academic Affiliation	Chemistry
Non-Academic Affiliation	Oregon State University. Graduate School
Subject	Rearrangements (Chemistry)
Rights Statement	Copyright Not Evaluated
Publisher	Oregon State University
Peer Reviewed	No
Language	English [eng]
Digitization Specifications	File scanned at 300 ppi (Monochrome) using Capture Perfect 3.0.82 on a Canon DR-9080C in PDF format. CVista PdfCompressor 4.0 was used for pdf compression and textual OCR.
Replaces	http://hdl.handle.net/1957/44425

Parents:

This work has no parents.

In Collection:

Thumbnail	Title	Date Uploaded	Visibility	Actions
	BolestaRichard1976.pdf	2017-08-23	Public	Download