Notes- A Convenient Method for Reduction of Hydroperoxide Ozonation Products

Knowles, William S.; Thompson, Quentin E.

doi:10.1021/jo01076a044

Cited by 54 publications

(15 citation statements)

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“…At the end of the 1950s, Knowles turned back to his old mathematics roots and became involved with kinetic studies, mostly for making simple aromatic molecules (10)(11)(12). He cites this research work as some of his most noteworthy because of the value it provided for Monsanto and the chemical industry.…”

Section: Kinetics Of Efficiencymentioning

confidence: 99%

Profile of William S. Knowles

Yun¹

2005

Proc. Natl. Acad. Sci. U.S.A.

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Section: Kinetics Of Efficiencymentioning

confidence: 99%

Profile of William S. Knowles

Yun¹

2005

Proc. Natl. Acad. Sci. U.S.A.

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“…The acetonide was cleaved to the glycol, and ring opening with lead tetracetate gave the expected dialdehyde which was cyclized to 162. This ring contraction was later improved considerably by subjecting the A 16 -olefin to ozone in the presence of trimethyl phosphite [117].…”

Section: Woodward Synthesismentioning

confidence: 99%

Cd → BCD → Abcd

1974

Organic Chemistry: A Series of Monographs

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The starting CD intermediates for the various total syntheses outlined in this chapter and in Chapter 7 are often the same or quite analogous. Historically, a large effort has been expended in the preparation of such material, both in the context of steroid synthesis and, recently, as a goal unto itself. A discussion of the pathways developed for the synthesis of CD intermediates has been included at this point such that later, when the individual total synthetic schemes are presented, it will be unnecessary to outline the preparation of the starting materials, except in those cases where unique pathways have been developed.Most of the early synthetic plans started with appropriate naphthalene derivatives which in turn gave rise to D-homosteroids. For example, Johnson's estrone synthesis started with decalin-l,5-dione (3, Scheme 12-1) which had earlier been prepared from 1,5-dihydroxynaphthalene (58%) [1], By modifying the previously employed conditions to include Raney nickel hydrogénation at elevated temperatures and pressures in a basic ethanolic solution, it was possible to obtain a mixture of diols, 2 (stereochemistry undetermined), which, without purification, could be oxidized to a mixture of eis and trans diketones 3 [2], The yield for this conversion (l-»3) was 55% and, for synthetic purposes, the mixture 239 O OH J Φ-,ύ^.

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“…When combined with reduction and oxidation, it has much potential for chemical synthesis [6][7][8]. Ozone reactions with alkene substrates are also of importance for chemistry of the atmosphere [9][10][11][12][13] including smog production [14] and various processes in the troposphere [14][15][16].…”

Section: Introductionmentioning

confidence: 99%