Michael reaction of [alpha]-chloro sulfonyl carbanion
Issued Date
2024
Copyright Date
1989
Resource Type
Language
eng
File Type
application/pdf
No. of Pages/File Size
iv, 145 leaves : ill.
Access Rights
open access
Rights
ผลงานนี้เป็นลิขสิทธิ์ของมหาวิทยาลัยมหิดล ขอสงวนไว้สำหรับเพื่อการศึกษาเท่านั้น ต้องอ้างอิงแหล่งที่มา ห้ามดัดแปลงเนื้อหา และห้ามนำไปใช้เพื่อการค้า
Rights Holder(s)
Mahidol University
Bibliographic Citation
Thesis (M.Sc. (Organic Chemistry))--Mahidol University, 1993
Suggested Citation
Chongkon Sumpanwatanakun Michael reaction of [alpha]-chloro sulfonyl carbanion. Thesis (M.Sc. (Organic Chemistry))--Mahidol University, 1993. Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/101015
Title
Michael reaction of [alpha]-chloro sulfonyl carbanion
Alternative Title(s)
ปฏิกิริยาไมเคิลของอัลฟา-คลอโร ซัลโฟนิล คาร์แบนอิออน
Author(s)
Advisor(s)
Abstract
The purpose of this research is to study the reaction of α-chloaro sulfonyl carbanion with various α,β-unsaturated compounds of monoesters, diesters, mononitrile, dinitrile, aldehydes, ketones, 1,3-ketorster, and 1,3-diketone. The two method for generating the α-chloro sulfonyl carbanion were investigates i.e. : 1. Lithium diisopropylamide (LDA) in tetrahydrofuran (THF) with hexamethylphosphoramide (HMPA) as a cobolvent (LDA method) 2. K(,2)Co(,3)/ benzyltriethylammonium chloride (TEBA) / aprotic solvent (PTC method) The results from the investigations could be summarized as follows : 1. Reaction of lithio chlormethyl phenyl sulfone anion with alpha, beta-unsaturated monoesters, diesters, mono and dinitrile gave the corresponding cyclopanes. 2. Reaction of alpha-chloro sulfonyl carbaion with methyl acrylate and crotonitrile yielded the cyclopentyl products in low yields. These products derived from a 1+2+2 MIMI-RC reaction. The reaction of methyl acrylate with alpha-chloro sulfonyl carbanion gave cyclohexyl derivative. This product could derived from a Michael-Michael-Dieckmann reaction. 3. The products from the reaction of α-chloro sulfonyl carbanion with α,β-unsaturated ketones depended no the tpye of ketones. The results obtained as follows.a. Methyl vinyl ketone, the major products are the corresponding cyclopropane and cyclohexyl compounds derived from Michael-Michael-Aldol reaction.b. Chalcone gave cyclopropanes and cyclopropyl epoxide.c. Dibenzalacetone, only cyclopropyl products were isolated.d. Cyclopentenone and cyclohexennone yielded cyclopropyl derivatives and the tricyclic compounds. These reactions provide a quick entry to polycyclic compounds. 4. The addition of lithio chloromethyl phenyl sulfone anion to α,β-unsaturated aldehydes gave 1,2-addition product exclusively. 5. The reaction of α,β-unsaturated 1,3-ketoester with lithio chloromethyl phenyl sulfone anion gave the expected cyclopropane in good yield. For α,β-unsaturated 1,3-diketone, dihydrofuran derivative was isolated in high yield.
Description
Organic Chemistry (Mahidol University 1993)
Degree Name
Master of Science
Degree Level
Master's degree
Degree Department
Faculty of Science
Degree Discipline
Organic Chemistry
Degree Grantor(s)
Mahidol University
