1995 Merck Frosst Award Lecture Quinone methides: relevant intermediates in organic chemistry
نویسندگان
چکیده
منابع مشابه
Quinone methides: useful reactive intermediates for DNA cross-linking and organic synthesis
We investigated the reactivity of several quinone methides (QMs) as activatable bis-alkylating agents capable of DNA cross-linking (XL-DNA) with promising potency. Taking advantage from a photochemical activation protocol of BINOL-derivatives, we had developed a new method for the resolution of 3,3’-CH2Xdisubstituted BINOL (X = NR2, SR, OH) studying as well the effect of electron-donating and e...
متن کاملQuinone methide intermediates in organic photochemistry*
Quinone methides are widely encountered reactive intermediates in the chemistry of phenols and related compounds. This paper summarizes our recent progress in uncovering new and general photochemical methods for forming quinone methides of various structural types in aqueous solution. Their mechanism of formation and subsequent chemistry are also discussed. New examples of excited-state intramo...
متن کاملNew reactive intermediates in organic chemistry
Physical organic chemistry (POC) and reactive intermediate chemistry (RIC) belong to the core subjects of organic chemistry. During the 1990s and 2000s both had become increasingly less fashionable, and in many countries, the mass of active researchers working in POC and RIC was in danger of becoming subcritical. Consequently, in 2003, the WhitesidesReport on the status of chemistry in Great Br...
متن کاملThe Domestication of ortho-Quinone Methides
CONSPECTUS: An ortho-quinone methide (o-QM) is a highly reactive chemical motif harnessed by nature for a variety of purposes. Given its extraordinary reactivity and biological importance, it is surprising how few applications within organic synthesis exist. We speculate that their widespread use has been slowed by the complications that surround the preparation of their precursors, the harsh g...
متن کاملThe Emergence of Quinone Methides in Asymmetric Organocatalysis.
Quinone methides (QMs) are highly reactive compounds that have been defined as "elusive" intermediates, or even as a "synthetic enigma" in organic chemistry. Indeed, there were just a handful of examples of their utilization in catalytic asymmetric settings until some years ago. This review collects organocatalytic asymmetric reactions that employ QMs as substrates and intermediates, from the e...
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ژورنال
عنوان ژورنال: Canadian Journal of Chemistry
سال: 1996
ISSN: 0008-4042,1480-3291
DOI: 10.1139/v96-051