Phase transfer catalysis in the tert-butyloxycarbonylation of alcohols, phenols, enols, and thiols with di-tert-butyl dicarbonate

Abstract

It is shown that the tert-butyloxycarbonylation of phenols, alcohols, enols, and thiols can be accomplished by reaction of these functionalities with di-tert-butyl dicarbonate under phase transfer conditions. The reactions proceed in high yield and can also be used for the introduction of t-BOC groups onto functionalized polymer backbones such as novolac or poly(p-hydroxystyrene). In addition, a study is made of the selectivity towards tert-butyloxycarbonylation of various polyfunctional compounds.

Cashew nut shell liquid based t‐BOC protected alternating “high ortho” copolymer as a possible e‐beam resist: Characterization using multi‐dimensional NMR spectroscopy

“…11,13 Two gram (3.3 mmol) of the novolac resin was mixed with 820 mg of di-t-butyl dicarbonate (97%, 3.6 mmol), 500 mg of anhydrous K 2 CO 3 (3.6 mmol), 10 mg of 18-crown-6 and stirred vigorously with 40 mL of THF for 3 days at room temperature. The reaction mixture was diluted with acetone (60 mL) and precipitated in water (800 mL).…”

“…Poly[p-((tert-butoxycarbonyl) oxy) styrene] has been used as a polymer matrix for this purpose. [8][9][10][11] These form the third generation of photoresists. The application of t-BOC derivative of novolac resins as DUV resists has been reported.…”

Inhibition and Promotion Efficiency of Bis-phenol Type Dissolution Inhibitors During Development.

“…The acid-sensitive t-Boc derivatives of bis-phenols used in this experiment were synthesized as described in the literature [8]. Bis-phenols were obtained from Honshu Kagaku Co. Ltd.…”

A simple and eco-sustainable method for theO-Boc protection/deprotection of various phenolic structures under water-mediated/catalyst-free conditions

“…The introduction of Boc moiety into phenols is generally achieved by the reaction of (Boc) 2 O in the presence of a phase transfer catalyst [7], 4-dimethylaminopyridine (DMAP) as catalyst [8] and using Lewis acids such as BiCl 3 [9], Zn(OAc) 2 [10], 1-tertbutoxy-2-tert-butoxycarbonyl-1,2-dihydroisoquinoline (BBDI) [3,4] and NaTiO 4 [11], or using 6,7-dimethoxyisoquinoline [12] as an organocatalyst.…”